6,7,8,9-Tetra-hydro-4b,9b-dihy-droxy-indano[1,2-b]indoline-9,10-dione monohydrate.

In the title compound, C(15)H(13)NO(4)·H(2)O, the organic mol-ecule adopts a V-shaped conformation in which the dihedral angle between the five-membered rings is 68.33 (5)°. The cyclo-hexenone ring adopts an envelope conformation, with one of the methyl-ene C atoms displaced by 0.607 (4) Å from the plane through the other atoms. In the crystal, inter-molecular N-H⋯(O,O) and O-H⋯O hydrogen bonds link the components into (001) sheeets and C-H⋯O inter-actions and aromatic π-π stacking [centroid-centroid separation = 3.6176 (19) Å] help to consolidate the packing.

Related literature

For background to ninhydrin, see: Friedman (1967 ▶); Moubasher (1948 ▶). For a related structure, see: Black et al. (1994 ▶).

Experimental

Crystal data

C15H13NO4·H2O

M = 289.28

Orthorhombic,

a = 10.703 (2) Å

b = 13.275 (4) Å

c = 19.683 (5) Å

V = 2796.6 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.30 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.970, T max = 0.978

17463 measured reflections

2532 independent reflections

1576 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.135

S = 1.08

2532 reflections

206 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025328/hb5521sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025328/hb5521Isup2.hkl

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

C15H13NO4·H2O	F(000) = 1216
Mr = 289.28	Dx = 1.369 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1576 reflections
a = 10.703 (2) Å	θ = 2.7–25.3°
b = 13.275 (4) Å	µ = 0.10 mm−1
c = 19.683 (5) Å	T = 296 K
V = 2796.6 (12) Å3	Prism, colourless
Z = 8	0.30 × 0.22 × 0.18 mm

Bruker Kappa APEXII CCD diffractometer	2532 independent reflections
Radiation source: fine-focus sealed tube	1576 reflections with I > 2σ(I)
graphite	Rint = 0.066
Detector resolution: 8.20 pixels mm-1	θmax = 25.5°, θmin = 2.7°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
Tmin = 0.970, Tmax = 0.978	l = −23→23
17463 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0498P)2 + 1.2061P] where P = (Fo2 + 2Fc2)/3
2532 reflections	(Δ/σ)max = 0.001
206 parameters	Δρmax = 0.20 e Å−3
2 restraints	Δρmin = −0.20 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

	x	y	z	Uiso*/Ueq
O1	0.6918 (2)	−0.15555 (15)	0.11236 (10)	0.0602 (8)
O2	0.91068 (17)	−0.08706 (14)	0.03362 (9)	0.0464 (7)
O3	0.64800 (18)	−0.14565 (14)	−0.04188 (10)	0.0540 (7)
O4	0.98666 (17)	0.09354 (16)	0.09227 (9)	0.0498 (7)
N1	0.8012 (2)	0.15460 (17)	0.04090 (11)	0.0402 (7)
C1	0.7997 (2)	0.0847 (2)	0.15639 (13)	0.0416 (9)
C2	0.8110 (3)	0.1600 (2)	0.20487 (14)	0.0563 (11)
C3	0.7442 (4)	0.1498 (3)	0.26471 (15)	0.0681 (13)
C4	0.6683 (3)	0.0675 (3)	0.27637 (16)	0.0692 (13)
C5	0.6593 (3)	−0.0089 (3)	0.22942 (14)	0.0582 (11)
C6	0.7266 (2)	0.0012 (2)	0.16905 (12)	0.0430 (9)
C7	0.7359 (2)	−0.07177 (19)	0.11328 (13)	0.0400 (9)
C8	0.8128 (2)	−0.02380 (18)	0.05584 (12)	0.0366 (8)
C9	0.7294 (2)	0.00822 (18)	−0.00174 (12)	0.0330 (8)
C10	0.6574 (2)	−0.0522 (2)	−0.04613 (13)	0.0395 (9)
C11	0.5833 (3)	0.0030 (2)	−0.10052 (14)	0.0482 (10)
C12	0.6310 (3)	0.1070 (2)	−0.11767 (14)	0.0518 (10)
C13	0.6515 (3)	0.16996 (19)	−0.05470 (13)	0.0450 (9)
C14	0.7286 (2)	0.11153 (18)	−0.00559 (12)	0.0353 (8)
C15	0.8580 (2)	0.08050 (19)	0.08678 (12)	0.0382 (8)
O5	0.4998 (3)	0.2705 (2)	0.12020 (14)	0.0943 (11)
H1	0.808 (2)	0.220 (2)	0.0473 (13)	0.0483*
H2	0.86192	0.21568	0.19739	0.0676*
H2A	0.932 (3)	−0.129 (2)	0.0658 (15)	0.0556*
H3	0.75062	0.19956	0.29781	0.0817*
H4	0.62257	0.06369	0.31648	0.0830*
H4A	1.018 (3)	0.085 (2)	0.0537 (15)	0.0597*
H5	0.61011	−0.06532	0.23762	0.0701*
H11A	0.58359	−0.03738	−0.14158	0.0578*
H11B	0.49724	0.00876	−0.08548	0.0578*
H12A	0.57126	0.14056	−0.14700	0.0621*
H12B	0.70914	0.10108	−0.14231	0.0621*
H13A	0.69391	0.23208	−0.06659	0.0540*
H13B	0.57173	0.18695	−0.03431	0.0540*
H51	0.452 (3)	0.224 (2)	0.0954 (17)	0.1131*
H52	0.526 (4)	0.239 (3)	0.1564 (14)	0.1131*

	U11	U22	U33	U12	U13	U23
O1	0.0834 (15)	0.0458 (13)	0.0515 (13)	−0.0033 (11)	0.0135 (11)	0.0065 (10)
O2	0.0484 (11)	0.0525 (12)	0.0382 (11)	0.0207 (9)	0.0053 (9)	0.0057 (9)
O3	0.0633 (13)	0.0389 (11)	0.0598 (13)	−0.0041 (9)	−0.0089 (10)	−0.0009 (10)
O4	0.0396 (11)	0.0760 (14)	0.0337 (10)	−0.0043 (9)	−0.0021 (8)	−0.0020 (10)
N1	0.0501 (13)	0.0359 (12)	0.0347 (12)	−0.0002 (10)	−0.0058 (10)	0.0002 (10)
C1	0.0455 (15)	0.0480 (17)	0.0314 (14)	0.0096 (13)	−0.0008 (12)	0.0009 (12)
C2	0.077 (2)	0.0570 (19)	0.0349 (16)	0.0064 (16)	−0.0027 (15)	−0.0028 (14)
C3	0.099 (3)	0.068 (2)	0.0373 (18)	0.020 (2)	−0.0008 (18)	−0.0101 (16)
C4	0.073 (2)	0.097 (3)	0.0377 (17)	0.015 (2)	0.0149 (16)	0.0000 (18)
C5	0.0555 (19)	0.080 (2)	0.0392 (16)	0.0044 (16)	0.0089 (14)	0.0058 (16)
C6	0.0424 (16)	0.0544 (17)	0.0321 (14)	0.0108 (13)	0.0018 (12)	0.0031 (13)
C7	0.0449 (15)	0.0399 (16)	0.0352 (15)	0.0082 (12)	0.0020 (12)	0.0054 (12)
C8	0.0376 (14)	0.0393 (14)	0.0328 (14)	0.0089 (11)	0.0035 (11)	0.0011 (11)
C9	0.0342 (13)	0.0357 (14)	0.0291 (12)	0.0029 (11)	0.0013 (10)	0.0014 (10)
C10	0.0373 (15)	0.0454 (16)	0.0357 (14)	0.0021 (12)	0.0034 (12)	−0.0018 (12)
C11	0.0462 (16)	0.0570 (18)	0.0414 (16)	0.0024 (14)	−0.0084 (13)	−0.0042 (14)
C12	0.0590 (18)	0.0549 (18)	0.0415 (16)	0.0024 (14)	−0.0110 (14)	0.0083 (14)
C13	0.0486 (16)	0.0420 (16)	0.0445 (16)	0.0051 (12)	−0.0083 (13)	0.0063 (12)
C14	0.0347 (14)	0.0417 (15)	0.0296 (13)	0.0015 (11)	0.0030 (11)	0.0009 (11)
C15	0.0385 (15)	0.0460 (16)	0.0301 (13)	0.0030 (12)	−0.0009 (11)	0.0001 (11)
O5	0.122 (2)	0.090 (2)	0.0708 (18)	−0.0540 (17)	−0.0238 (16)	0.0200 (14)

O1—C7	1.208 (3)	C7—C8	1.537 (3)
O2—C8	1.412 (3)	C8—C9	1.504 (3)
O3—C10	1.247 (3)	C8—C15	1.588 (3)
O4—C15	1.392 (3)	C9—C14	1.374 (3)
O2—H2A	0.87 (3)	C9—C10	1.414 (3)
O4—H4A	0.84 (3)	C10—C11	1.521 (4)
O5—H51	0.94 (3)	C11—C12	1.510 (4)
O5—H52	0.87 (3)	C12—C13	1.511 (4)
N1—C14	1.330 (3)	C13—C14	1.489 (4)
N1—C15	1.467 (3)	C2—H2	0.9300
N1—H1	0.88 (3)	C3—H3	0.9300
C1—C6	1.380 (4)	C4—H4	0.9300
C1—C2	1.387 (4)	C5—H5	0.9300
C1—C15	1.507 (3)	C11—H11B	0.9700
C2—C3	1.385 (4)	C11—H11A	0.9700
C3—C4	1.381 (6)	C12—H12A	0.9700
C4—C5	1.376 (5)	C12—H12B	0.9700
C5—C6	1.396 (4)	C13—H13B	0.9700
C6—C7	1.467 (4)	C13—H13A	0.9700
C8—O2—H2A	110 (2)	C12—C13—C14	109.0 (2)
C15—O4—H4A	108 (2)	N1—C14—C13	123.1 (2)
H51—O5—H52	107 (3)	N1—C14—C9	112.8 (2)
C14—N1—C15	112.2 (2)	C9—C14—C13	124.0 (2)
C15—N1—H1	122.6 (16)	N1—C15—C8	102.84 (18)
C14—N1—H1	124.8 (16)	C1—C15—C8	104.77 (19)
C2—C1—C6	120.3 (2)	O4—C15—N1	112.0 (2)
C2—C1—C15	128.0 (2)	O4—C15—C1	109.54 (19)
C6—C1—C15	111.7 (2)	N1—C15—C1	111.31 (19)
C1—C2—C3	118.0 (3)	O4—C15—C8	116.07 (19)
C2—C3—C4	121.5 (3)	C1—C2—H2	121.00
C3—C4—C5	120.9 (3)	C3—C2—H2	121.00
C4—C5—C6	117.7 (3)	C4—C3—H3	119.00
C5—C6—C7	127.5 (3)	C2—C3—H3	119.00
C1—C6—C5	121.6 (3)	C3—C4—H4	120.00
C1—C6—C7	110.9 (2)	C5—C4—H4	120.00
C6—C7—C8	108.3 (2)	C4—C5—H5	121.00
O1—C7—C6	126.3 (2)	C6—C5—H5	121.00
O1—C7—C8	125.4 (2)	C10—C11—H11B	109.00
O2—C8—C9	112.03 (19)	C12—C11—H11A	109.00
O2—C8—C7	112.26 (19)	C12—C11—H11B	108.00
C7—C8—C9	110.71 (18)	H11A—C11—H11B	108.00
C7—C8—C15	104.02 (19)	C10—C11—H11A	109.00
C9—C8—C15	102.91 (19)	C11—C12—H12B	109.00
O2—C8—C15	114.29 (18)	C13—C12—H12A	109.00
C8—C9—C14	109.1 (2)	C11—C12—H12A	109.00
C10—C9—C14	121.9 (2)	H12A—C12—H12B	108.00
C8—C9—C10	129.0 (2)	C13—C12—H12B	109.00
O3—C10—C9	124.5 (2)	C12—C13—H13A	110.00
O3—C10—C11	119.0 (2)	C12—C13—H13B	110.00
C9—C10—C11	116.5 (2)	C14—C13—H13B	110.00
C10—C11—C12	114.9 (2)	H13A—C13—H13B	108.00
C11—C12—C13	111.8 (2)	C14—C13—H13A	110.00
C15—N1—C14—C9	−3.2 (3)	C6—C7—C8—C15	5.2 (2)
C15—N1—C14—C13	174.7 (2)	O2—C8—C9—C10	60.0 (3)
C14—N1—C15—O4	129.3 (2)	O2—C8—C9—C14	−121.6 (2)
C14—N1—C15—C1	−107.7 (2)	C7—C8—C9—C10	−66.1 (3)
C14—N1—C15—C8	4.0 (2)	C7—C8—C9—C14	112.3 (2)
C6—C1—C2—C3	−1.9 (4)	C15—C8—C9—C10	−176.7 (2)
C15—C1—C2—C3	177.3 (3)	C15—C8—C9—C14	1.7 (2)
C2—C1—C6—C5	2.0 (4)	O2—C8—C15—O4	−4.1 (3)
C2—C1—C6—C7	−175.7 (2)	O2—C8—C15—N1	118.5 (2)
C15—C1—C6—C5	−177.3 (2)	O2—C8—C15—C1	−125.1 (2)
C15—C1—C6—C7	5.1 (3)	C7—C8—C15—O4	118.6 (2)
C2—C1—C15—O4	54.1 (3)	C7—C8—C15—N1	−118.75 (19)
C2—C1—C15—N1	−70.3 (3)	C7—C8—C15—C1	−2.3 (2)
C2—C1—C15—C8	179.3 (2)	C9—C8—C15—O4	−125.8 (2)
C6—C1—C15—O4	−126.7 (2)	C9—C8—C15—N1	−3.2 (2)
C6—C1—C15—N1	108.9 (2)	C9—C8—C15—C1	113.25 (19)
C6—C1—C15—C8	−1.5 (3)	C8—C9—C10—O3	3.4 (4)
C1—C2—C3—C4	0.0 (5)	C8—C9—C10—C11	−179.2 (2)
C2—C3—C4—C5	1.9 (6)	C14—C9—C10—O3	−174.8 (2)
C3—C4—C5—C6	−1.8 (5)	C14—C9—C10—C11	2.6 (3)
C4—C5—C6—C1	−0.1 (4)	C8—C9—C14—N1	0.8 (3)
C4—C5—C6—C7	177.1 (3)	C8—C9—C14—C13	−177.1 (2)
C1—C6—C7—O1	173.0 (2)	C10—C9—C14—N1	179.3 (2)
C1—C6—C7—C8	−6.5 (3)	C10—C9—C14—C13	1.4 (4)
C5—C6—C7—O1	−4.4 (4)	O3—C10—C11—C12	−160.4 (2)
C5—C6—C7—C8	176.1 (3)	C9—C10—C11—C12	22.0 (3)
O1—C7—C8—O2	−50.3 (3)	C10—C11—C12—C13	−49.8 (3)
O1—C7—C8—C9	75.7 (3)	C11—C12—C13—C14	50.8 (3)
O1—C7—C8—C15	−174.4 (2)	C12—C13—C14—N1	153.7 (2)
C6—C7—C8—O2	129.2 (2)	C12—C13—C14—C9	−28.7 (3)
C6—C7—C8—C9	−104.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88 (3)	2.09 (3)	2.887 (3)	150 (2)
N1—H1···O3i	0.88 (3)	2.55 (3)	3.159 (3)	127 (2)
O2—H2A···O5ii	0.87 (3)	1.86 (3)	2.720 (3)	168 (3)
O4—H4A···O2iii	0.84 (3)	1.88 (3)	2.712 (3)	171 (3)
O5—H51···O3iv	0.94 (3)	1.83 (3)	2.762 (4)	174 (3)
C2—H2···O1i	0.93	2.46	3.052 (3)	122
C4—H4···O4v	0.93	2.34	3.253 (4)	165
C13—H13A···O3i	0.97	2.39	3.265 (4)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88 (3)	2.09 (3)	2.887 (3)	150 (2)
N1—H1⋯O3i	0.88 (3)	2.55 (3)	3.159 (3)	127 (2)
O2—H2A⋯O5ii	0.87 (3)	1.86 (3)	2.720 (3)	168 (3)
O4—H4A⋯O2iii	0.84 (3)	1.88 (3)	2.712 (3)	171 (3)
O5—H51⋯O3iv	0.94 (3)	1.83 (3)	2.762 (4)	174 (3)
C2—H2⋯O1i	0.93	2.46	3.052 (3)	122
C4—H4⋯O4v	0.93	2.34	3.253 (4)	165
C13—H13A⋯O3i	0.97	2.39	3.265 (4)	149

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .