Resorcinol ninhydrin complex: 1,5,9-trihy­droxy-8-oxatetra­cyclo­[7.7.0.02,7.010,15]hexa­deca-2,4,6,10(15),11,13-hexaen-16-one

Devi, T.U.; Priya, S.; Kalpana, G.; Selvanayagam, S.; Sridhar, B.

doi:10.1107/S1600536812014249

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1323

doi:10.1107/S1600536812014249

Open

access

Resorcinol ninhydrin complex: 1,5,9-trihydroxy-8-oxatetracyclo[7.7.0.0^2,7.0^10,15]hexadeca-2,4,6,10(15),11,13-hexaen-16-one

T. Uma Devi,^a S. Priya,^b G. Kalpana,^c S. Selvanayagam ^d ^* and B. Sridhar ^e

^aDepartment of Physics, Government Arts College for Women, Pudukkottaii 622 001, India, ^bDepartment of Physics, Cauvery College for Women, Tiruchirappalli 620 018, India, ^cDepartment of Physics, Shivani Institute of Technology, Tiruchirappalli 620 009, India, ^dDepartment of Physics, Kalasalingam University, Krishnankoil 626 126, India, and ^eLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India
^*Correspondence e-mail: s_selvanayagam@rediffmail.com

(Received 30 March 2012; accepted 2 April 2012; online 6 April 2012)

In the title compound, C₁₅H₁₀O₅, the cyclopentanone (r.m.s. deviation = 0.049 Å) and oxolane (r.m.s. deviation = 0.048 Å) rings make a dihedral angle of 67.91 (4)°. An intramolecular O—H⋯O hydrogen bond is observed. In the crystal, molecules associate via O—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For general background to ninhydrin derivatives, see: Hansen & Joullie (2005 ); Leane et al. (2004 ). For general background to resorcinol derivatives, see: Chen et al. (2011 ); Bao et al. (2010 ); Zheng & Wu (2007 ).

Experimental

Crystal data

C₁₅H₁₀O₅
M_r = 270.23
Monoclinic, P 2₁ /c
a = 9.1117 (5) Å
b = 12.2995 (7) Å
c = 10.1177 (5) Å
β = 91.837 (1)°
V = 1133.30 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 292 K
0.22 × 0.20 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
12939 measured reflections
2699 independent reflections
2468 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.106
S = 1.05
2699 reflections
221 parameters
All H-atom parameters refined
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O3ⁱ	0.90 (2)	2.02 (2)	2.877 (1)	158 (2)
O3—H3A⋯O4ⁱⁱ	0.89 (2)	2.18 (2)	3.013 (1)	157 (2)
O2—H2A⋯O1ⁱⁱⁱ	0.87 (2)	1.92 (2)	2.746 (1)	159 (2)
O3—H3A⋯O2	0.89 (2)	2.33 (2)	2.667 (1)	102 (1)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812014249/bt5867sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014249/bt5867Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812014249/bt5867Isup3.cml

checkCIF report

Comment top

Resorcinol derivatives posses cytotoxity (Zheng & Wu, 2007; Bao et al., 2010) and antitumor activities (Chen et al., 2011). Ninhydrin analogue was found to be an important reagent to develop finger prints on porous surface (Hansen & Joullie, 2005). Ninhydrin assay is an essential aid in the design and testing of solid dosage forms with different chitosan-drug release profiles (Leane et al., 2004).In view of these importance on ninhydrin and resorcinol derivatives, we have undertaken the crystal structure determination of the present complex, and the results are presented here.

The X-ray study confirmed the molecular structure and atomic connectivity for (I), as illustrated in Fig. 1.

The plane calculation revealed that the benzene, cyclopentanone, oxolane and phenyl rings are in planar. Atoms O1, O2 and O3 deviate by 0.235 (1), 0.916 (1) and 1.166 (1) Å, respectively with respect to the fused rings of benzene and cyclopentanone. Atoms O2, O3 and O4 deviate by -1.127 (1), -0.801 (1) and 0.091 (1) Å, respectively with respect to the fused rings of oxolane and phenyl rings. The dihedral angle between the two half of the molecule with respect to C8-C9 bond is 1.5 (1)°.

The molecular structure is influenced by an intramolecular O—H···O hydrogen bonds. In the molecular packing, O—H···O hydrogen bonds involving atoms O3 and O4 link inversion-related molecules to form R₂² (16) graph-set dimer. (Fig. 2 and Table 1). In addition to this atoms, O2 and C11 form a R₂²(10) graph-set motif in the unit cell with the help of intermolecular hydrogen bonds (Fig.3). A C(8) chain motif is formed in the unit cell with the help of O—H···O hydrogen bonds involving atoms O4 and O3 which results the helical shape arrangement along bc plane of the unit cell (Fig. 4).

Related literature top

For general background to ninhydrin derivatives, see: Hansen & Joullie (2005); Leane et al. (2004). For general background to resorcinol derivatives, see: Chen et al. (2011); Bao et al. (2010); Zheng & Wu (2007).

Experimental top

A mixture of ninhydrin and resorcinol in molar ratio 1:1 were dissolved in dilute acetic medium and stirred well using a temperature controlled magnetic stirrer to yield a homogeneous mixture of solution. Then the solution was allowed to evaporate at room temperature, which yielded a crystalline adduct. Single crystals were grown by slow evaporation from ethanol.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level
	Fig. 2. Molecular packing of the title compound, viewed along the a axis; H-bonds are shown as dashed lines forms a R₂²(16) dimers in unit cell. For the sake of clarity, H atoms, not involved in hydrogen bonds, have been omitted
	Fig. 3. Molecular packing of the title compound, viewed along the b axis; H-bonds are shown as dashed lines forms a R₂²(10) dimers in unit cell. For the sake of clarity, H atoms, not involved in hydrogen bonds, have been omitted
	Fig. 4. Molecular packing of the title compound, viewed along the c axis; H-bonds are shown as dashed lines forms a C(8) chain-motif in unit cell. For the sake of clarity, H atoms, not involved in hydrogen bonds, have been omitted

1,5,9-trihydroxy-8-oxatetracyclo[7.7.0.0^2,7.0^10,15]hexadeca- 2,4,6,10 (15),11,13-hexaen-16-one top

Crystal data top

C₁₅H₁₀O₅	F(000) = 560
M_r = 270.23	D_x = 1.584 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8468 reflections
a = 9.1117 (5) Å	θ = 2.2–27.1°
b = 12.2995 (7) Å	µ = 0.12 mm⁻¹
c = 10.1177 (5) Å	T = 292 K
β = 91.837 (1)°	Block, colourless
V = 1133.30 (11) Å³	0.22 × 0.20 × 0.19 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2468 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 28.0°, θ_min = 2.2°
ω scans	h = −12→11
12939 measured reflections	k = −16→16
2699 independent reflections	l = −13→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	All H-atom parameters refined
S = 1.05	w = 1/[σ²(F_o²) + (0.0594P)² + 0.3056P] where P = (F_o² + 2F_c²)/3
2699 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₅H₁₀O₅	V = 1133.30 (11) Å³
M_r = 270.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.1117 (5) Å	µ = 0.12 mm⁻¹
b = 12.2995 (7) Å	T = 292 K
c = 10.1177 (5) Å	0.22 × 0.20 × 0.19 mm
β = 91.837 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2468 reflections with I > 2σ(I)
12939 measured reflections	R_int = 0.020
2699 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.106	All H-atom parameters refined
S = 1.05	Δρ_max = 0.31 e Å⁻³
2699 reflections	Δρ_min = −0.28 e Å⁻³
221 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.55633 (10)	0.40497 (9)	0.32526 (9)	0.0416 (2)
O2	0.38544 (11)	0.59167 (7)	0.40684 (9)	0.0382 (2)
H2A	0.394 (2)	0.5760 (16)	0.490 (2)	0.058 (5)*
O3	0.22262 (11)	0.65338 (7)	0.19634 (9)	0.0369 (2)
H3A	0.219 (2)	0.689 (2)	0.272 (2)	0.080 (7)*
O4	−0.12067 (11)	0.24783 (9)	0.55006 (10)	0.0444 (3)
H4A	−0.175 (2)	0.2263 (19)	0.479 (2)	0.076 (6)*
O5	0.07320 (9)	0.50826 (7)	0.24520 (8)	0.0336 (2)
C1	0.21080 (14)	0.48007 (11)	−0.02647 (12)	0.0345 (3)
H1	0.1252 (19)	0.5225 (14)	−0.0506 (16)	0.042 (4)*
C2	0.27738 (16)	0.41740 (12)	−0.12105 (13)	0.0409 (3)
H2	0.2341 (19)	0.4179 (14)	−0.2090 (18)	0.049 (4)*
C3	0.40256 (16)	0.35623 (11)	−0.09057 (14)	0.0418 (3)
H3	0.4472 (19)	0.3140 (14)	−0.1582 (17)	0.048 (4)*
C4	0.46396 (14)	0.35571 (10)	0.03612 (13)	0.0366 (3)
H4	0.5509 (18)	0.3132 (14)	0.0606 (15)	0.041 (4)*
C5	0.39742 (12)	0.41873 (10)	0.13132 (11)	0.0301 (2)
C6	0.27356 (12)	0.48078 (9)	0.10008 (11)	0.0285 (2)
C7	0.44307 (12)	0.43593 (10)	0.27024 (11)	0.0302 (2)
C8	0.32381 (12)	0.50301 (9)	0.33703 (11)	0.0283 (2)
C9	0.22170 (12)	0.54241 (9)	0.21795 (11)	0.0289 (2)
C10	0.22056 (12)	0.43138 (9)	0.41014 (11)	0.0278 (2)
C11	0.24218 (13)	0.36685 (10)	0.52153 (11)	0.0310 (2)
H11	0.3393 (17)	0.3619 (12)	0.5676 (15)	0.036 (4)*
C12	0.12568 (14)	0.30692 (10)	0.56731 (12)	0.0336 (3)
H12	0.1362 (17)	0.2601 (13)	0.6454 (16)	0.043 (4)*
C13	−0.01040 (13)	0.31088 (10)	0.50070 (12)	0.0328 (3)
C14	−0.03552 (13)	0.37657 (10)	0.39052 (12)	0.0331 (3)
H14	−0.1314 (18)	0.3805 (13)	0.3462 (15)	0.041 (4)*
C15	0.08212 (12)	0.43688 (10)	0.34892 (11)	0.0290 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0309 (4)	0.0562 (6)	0.0373 (5)	0.0065 (4)	−0.0056 (4)	0.0060 (4)
O2	0.0455 (5)	0.0369 (5)	0.0315 (5)	−0.0098 (4)	−0.0097 (4)	−0.0017 (4)
O3	0.0480 (5)	0.0302 (4)	0.0321 (5)	0.0039 (4)	−0.0046 (4)	0.0019 (3)
O4	0.0441 (5)	0.0478 (6)	0.0416 (5)	−0.0145 (4)	0.0066 (4)	−0.0008 (4)
O5	0.0264 (4)	0.0455 (5)	0.0288 (4)	0.0020 (3)	−0.0033 (3)	0.0050 (3)
C1	0.0349 (6)	0.0402 (6)	0.0281 (6)	−0.0044 (5)	−0.0046 (4)	0.0013 (5)
C2	0.0495 (7)	0.0471 (7)	0.0261 (6)	−0.0107 (6)	−0.0005 (5)	−0.0029 (5)
C3	0.0504 (8)	0.0396 (7)	0.0360 (7)	−0.0074 (6)	0.0106 (6)	−0.0079 (5)
C4	0.0357 (6)	0.0338 (6)	0.0408 (7)	−0.0013 (5)	0.0063 (5)	−0.0008 (5)
C5	0.0292 (5)	0.0319 (6)	0.0293 (6)	−0.0039 (4)	−0.0003 (4)	0.0019 (4)
C6	0.0293 (5)	0.0311 (5)	0.0250 (5)	−0.0044 (4)	−0.0006 (4)	0.0009 (4)
C7	0.0269 (5)	0.0333 (5)	0.0304 (6)	−0.0031 (4)	−0.0015 (4)	0.0047 (4)
C8	0.0288 (5)	0.0309 (5)	0.0249 (5)	−0.0016 (4)	−0.0051 (4)	0.0006 (4)
C9	0.0292 (5)	0.0316 (5)	0.0258 (5)	0.0004 (4)	−0.0031 (4)	0.0009 (4)
C10	0.0277 (5)	0.0310 (5)	0.0247 (5)	0.0002 (4)	−0.0006 (4)	−0.0026 (4)
C11	0.0322 (6)	0.0333 (6)	0.0272 (5)	0.0015 (4)	−0.0031 (4)	−0.0013 (4)
C12	0.0404 (6)	0.0321 (6)	0.0282 (6)	0.0005 (5)	0.0011 (5)	−0.0002 (4)
C13	0.0354 (6)	0.0323 (6)	0.0310 (6)	−0.0049 (5)	0.0061 (4)	−0.0067 (4)
C14	0.0284 (5)	0.0397 (6)	0.0310 (6)	−0.0016 (5)	−0.0011 (4)	−0.0055 (5)
C15	0.0297 (5)	0.0334 (6)	0.0239 (5)	0.0022 (4)	−0.0013 (4)	−0.0032 (4)

Geometric parameters (Å, º) top

O1—C7	1.2178 (14)	C4—H4	0.975 (17)
O2—C8	1.4063 (14)	C5—C6	1.3904 (16)
O2—H2A	0.87 (2)	C5—C7	1.4683 (16)
O3—C9	1.3823 (14)	C6—C9	1.5021 (16)
O3—H3A	0.89 (2)	C7—C8	1.5379 (16)
O4—C13	1.3756 (15)	C8—C10	1.5011 (16)
O4—H4A	0.90 (2)	C8—C9	1.5749 (15)
O5—C15	1.3686 (14)	C10—C11	1.3873 (16)
O5—C9	1.4516 (14)	C10—C15	1.3890 (15)
C1—C2	1.3839 (19)	C11—C12	1.3843 (17)
C1—C6	1.3855 (16)	C11—H11	0.989 (16)
C1—H1	0.964 (17)	C12—C13	1.3930 (18)
C2—C3	1.393 (2)	C12—H12	0.979 (17)
C2—H2	0.962 (18)	C13—C14	1.3899 (18)
C3—C4	1.382 (2)	C14—C15	1.3803 (17)
C3—H3	0.960 (17)	C14—H14	0.970 (16)
C4—C5	1.3907 (17)

C8—O2—H2A	109.8 (13)	O2—C8—C9	111.24 (9)
C9—O3—H3A	110.3 (15)	C10—C8—C9	101.15 (9)
C13—O4—H4A	105.4 (14)	C7—C8—C9	103.73 (9)
C15—O5—C9	107.37 (8)	O3—C9—O5	109.04 (9)
C2—C1—C6	117.74 (12)	O3—C9—C6	111.66 (9)
C2—C1—H1	119.7 (10)	O5—C9—C6	108.88 (9)
C6—C1—H1	122.5 (10)	O3—C9—C8	114.73 (9)
C1—C2—C3	121.46 (12)	O5—C9—C8	107.28 (9)
C1—C2—H2	117.4 (10)	C6—C9—C8	105.01 (9)
C3—C2—H2	121.1 (10)	C11—C10—C15	119.57 (11)
C4—C3—C2	120.81 (12)	C11—C10—C8	131.39 (10)
C4—C3—H3	119.4 (10)	C15—C10—C8	109.04 (10)
C2—C3—H3	119.8 (10)	C12—C11—C10	119.08 (11)
C3—C4—C5	117.86 (12)	C12—C11—H11	119.6 (9)
C3—C4—H4	122.6 (9)	C10—C11—H11	121.3 (9)
C5—C4—H4	119.5 (9)	C11—C12—C13	119.98 (11)
C6—C5—C4	121.15 (11)	C11—C12—H12	121.8 (9)
C6—C5—C7	109.97 (10)	C13—C12—H12	118.2 (9)
C4—C5—C7	128.83 (11)	O4—C13—C14	121.03 (11)
C1—C6—C5	120.97 (11)	O4—C13—C12	116.99 (11)
C1—C6—C9	127.29 (11)	C14—C13—C12	121.97 (11)
C5—C6—C9	111.73 (10)	C15—C14—C13	116.58 (11)
O1—C7—C5	127.04 (11)	C15—C14—H14	121.9 (9)
O1—C7—C8	124.56 (11)	C13—C14—H14	121.5 (9)
C5—C7—C8	108.39 (9)	O5—C15—C14	123.43 (10)
O2—C8—C10	117.01 (9)	O5—C15—C10	113.82 (10)
O2—C8—C7	111.12 (9)	C14—C15—C10	122.74 (11)
C10—C8—C7	111.37 (9)

C6—C1—C2—C3	0.49 (19)	O2—C8—C9—O3	5.95 (14)
C1—C2—C3—C4	0.4 (2)	C10—C8—C9—O3	130.92 (10)
C2—C3—C4—C5	−0.50 (19)	C7—C8—C9—O3	−113.58 (10)
C3—C4—C5—C6	−0.34 (18)	O2—C8—C9—O5	−115.34 (10)
C3—C4—C5—C7	−177.34 (12)	C10—C8—C9—O5	9.63 (11)
C2—C1—C6—C5	−1.33 (18)	C7—C8—C9—O5	125.13 (9)
C2—C1—C6—C9	179.74 (11)	O2—C8—C9—C6	128.92 (10)
C4—C5—C6—C1	1.28 (18)	C10—C8—C9—C6	−106.11 (10)
C7—C5—C6—C1	178.80 (10)	C7—C8—C9—C6	9.39 (11)
C4—C5—C6—C9	−179.63 (10)	O2—C8—C10—C11	−62.49 (17)
C7—C5—C6—C9	−2.12 (13)	C7—C8—C10—C11	66.83 (15)
C6—C5—C7—O1	−170.36 (12)	C9—C8—C10—C11	176.52 (12)
C4—C5—C7—O1	6.9 (2)	O2—C8—C10—C15	116.84 (11)
C6—C5—C7—C8	8.49 (13)	C7—C8—C10—C15	−113.83 (10)
C4—C5—C7—C8	−174.24 (11)	C9—C8—C10—C15	−4.14 (12)
O1—C7—C8—O2	48.37 (15)	C15—C10—C11—C12	1.69 (17)
C5—C7—C8—O2	−130.52 (10)	C8—C10—C11—C12	−179.04 (11)
O1—C7—C8—C10	−84.00 (14)	C10—C11—C12—C13	0.81 (18)
C5—C7—C8—C10	97.11 (10)	C11—C12—C13—O4	178.84 (11)
O1—C7—C8—C9	167.98 (11)	C11—C12—C13—C14	−2.16 (18)
C5—C7—C8—C9	−10.91 (11)	O4—C13—C14—C15	179.85 (11)
C15—O5—C9—O3	−136.72 (9)	C12—C13—C14—C15	0.90 (18)
C15—O5—C9—C6	101.24 (10)	C9—O5—C15—C14	−170.98 (11)
C15—O5—C9—C8	−11.91 (12)	C9—O5—C15—C10	9.76 (13)
C1—C6—C9—O3	−60.94 (15)	C13—C14—C15—O5	−177.48 (10)
C5—C6—C9—O3	120.05 (11)	C13—C14—C15—C10	1.71 (17)
C1—C6—C9—O5	59.51 (15)	C11—C10—C15—O5	176.22 (10)
C5—C6—C9—O5	−119.51 (10)	C8—C10—C15—O5	−3.20 (13)
C1—C6—C9—C8	174.14 (11)	C11—C10—C15—C14	−3.04 (18)
C5—C6—C9—C8	−4.88 (12)	C8—C10—C15—C14	177.54 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3ⁱ	0.90 (2)	2.02 (2)	2.877 (1)	158 (2)
O3—H3A···O4ⁱⁱ	0.89 (2)	2.18 (2)	3.013 (1)	157 (2)
O2—H2A···O1ⁱⁱⁱ	0.87 (2)	1.92 (2)	2.746 (1)	159 (2)
O3—H3A···O2	0.89 (2)	2.33 (2)	2.667 (1)	102 (1)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀O₅
M_r	270.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	292
a, b, c (Å)	9.1117 (5), 12.2995 (7), 10.1177 (5)
β (°)	91.837 (1)
V (Å³)	1133.30 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.22 × 0.20 × 0.19

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12939, 2699, 2468
R_int	0.020

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.106, 1.05
No. of reflections	2699
No. of parameters	221
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.28

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3ⁱ	0.90 (2)	2.02 (2)	2.877 (1)	158 (2)
O3—H3A···O4ⁱⁱ	0.89 (2)	2.18 (2)	3.013 (1)	157 (2)
O2—H2A···O1ⁱⁱⁱ	0.87 (2)	1.92 (2)	2.746 (1)	159 (2)
O3—H3A···O2	0.89 (2)	2.33 (2)	2.667 (1)	102 (1)

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

Acknowledgements

SS acknowledges the Department of Science and Technology (DST), India, for providing computing facilities under the DST-Fast Track Scheme.

References

Bao, L., Wang, M., Zhao, F., Zhao, Y. & Liu, H. (2010). Chem. Biodivers. 7, 2901–2907. Web of Science CrossRef CAS PubMed Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, L. P., Zhao, F., Wang, Y., Zhao, L. L., Li, Q. P. & Liu, H. W. (2011). J. Asian. Nat. Prod. Res. 13, 734–743. Web of Science CrossRef CAS PubMed Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hansen, D. B. & Joullie, M. M. (2005). Chem. Soc. Rev. 34, 408–417. Web of Science CrossRef PubMed CAS Google Scholar
Leane, M. M., Nankervis, R., Smith, A. & Illum, L. (2004). Int. J. Pharm. 271, 241–249. 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zheng, Y. & Wu, F. E. (2007). J. Asian. Nat. Prod. Res. 9, 545–549. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1323

doi:10.1107/S1600536812014249

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Resorcinol ninhydrin complex: 1,5,9-trihy­dr­oxy-8-oxa­tetra­cyclo­[7.7.0.02,7.010,15]hexa­deca-2,4,6,10(15),11,13-hexaen-16-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Resorcinol ninhydrin complex: 1,5,9-trihydroxy-8-oxatetracyclo[7.7.0.0^2,7.0^10,15]hexadeca-2,4,6,10(15),11,13-hexaen-16-one