Resorcinol ninhydrin complex: 1,5,9-trihy-droxy-8-oxatetra-cyclo-[7.7.0.0(2,7).0(10,15)]hexa-deca-2,4,6,10(15),11,13-hexaen-16-one.

In the title compound, C(15)H(10)O(5), the cyclo-penta-none (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 intra-molecular O-H⋯O hydrogen bond is observed. In the crystal, mol-ecules 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 = 270.23

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.05

2699 reflections

221 parameters

All H-atom parameters refined

Δρmax = 0.31 e Å−3

Δρmin = −0.28 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812014249/bt5867sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812014249/bt5867Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H10O5	F(000) = 560
Mr = 270.23	Dx = 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

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

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(Fo2) + (0.0594P)2 + 0.3056P] where P = (Fo2 + 2Fc2)/3
2699 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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)

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) ; (ii) ; (iii) .