3a,8a-Dihy­droxy-1,3,3a,8a-tetra­hydro­indeno­[1,2-d]imidazole-2,8-dione

Ghalib, R.M.; Hashim, R.; Mehdi, S.H.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S1600536811019039

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1525

doi:10.1107/S1600536811019039

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3a,8a-Dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-dione

Raza Murad Ghalib,^a Rokiah Hashim,^a Sayed Hasan Mehdi,^a Ching Kheng Quah ^b ‡ and Hoong-Kun Fun ^b ^*§

^aSchool of Industrial Technology, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 10 May 2011; accepted 19 May 2011; online 25 May 2011)

In the title molecule, C₁₀H₈N₂O₄, the imidazolidine ring adopts a twisted conformation. In the crystal, the molecules are linked via a pair of bifurcated intermolecular O—H⋯O hydrogen bonds, forming an inversion dimer. The dimers are further linked via N—H⋯O hydrogen bonds into a tape along the b axis.

Related literature

For general background to and the properties of ninhydrinurea derivatives, see: Caputo et al. (1987 ); Kaupp et al. (2002 ); Sarra & Stephani (2000 ). For standard bond-length data, see: Allen et al. (1987 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₀H₈N₂O₄
M_r = 220.18
Triclinic, $[P \overline 1]$
a = 6.7914 (2) Å
b = 7.3201 (2) Å
c = 9.5006 (3) Å
α = 94.258 (1)°
β = 102.773 (1)°
γ = 93.725 (1)°
V = 457.74 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 296 K
0.39 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.952, T_max = 0.994
6684 measured reflections
2081 independent reflections
1634 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.110
S = 1.05
2081 reflections
177 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 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—H1O3⋯O1ⁱ	0.89 (3)	2.02 (3)	2.8653 (17)	158 (2)
O2—H1O2⋯O1ⁱ	0.95 (3)	1.89 (3)	2.8103 (17)	163 (2)
N2—H1N2⋯O4ⁱⁱ	0.83 (2)	2.454 (19)	3.1282 (19)	139.3 (18)
N1—H1N1⋯O4ⁱⁱⁱ	0.86 (2)	2.06 (2)	2.8841 (18)	159.4 (19)
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+2, -y, -z+2; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811019039/is2712sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019039/is2712Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019039/is2712Isup3.cml

checkCIF report

Comment top

The title compound ninhydrinurea (Caputo et al., 1987; Kaupp et al., 2002; Sarra & Stephani, 2000) has been synthesized by a new route.

In the title compound, Fig. 1, the imidazolidine ring (N1/N2/C1/C2/C10) is twisted about the N2—C10 bond with puckering parameters (Cremer & Pople, 1975) Q = 0.1107 (16) Å and Θ = 271.8 (8)° and its least-squares plane makes a dihedral angle of 62.18 (9)° with the benzene ring (C3–C8). Bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal packing, Fig. 2, the molecules are linked via intermolecular O3—H1O3···O1ⁱ, O2—H1O2···O1ⁱ, N2—H1N2···O4ⁱⁱ and N1—H1N1···O4ⁱⁱⁱ hydrogen bonds (Table 1) into one-dimensional chains along the [010] direction.

Related literature top

For general background to and the properties of ninhydrinurea derivatives, see: Caputo et al. (1987); Kaupp et al. (2002); Sarra & Stephani (2000). For standard bond-length data, see: Allen et al. (1987). For ring conformations, see: Cremer & Pople (1975).

Experimental top

A mixture of ninhydrin (1.78 g) and urea (0.60 g) in molar ratio 1:1 were well dissolved in acetic acid and then heated over a water bath for 15 minutes. The reaction mixture was dried on rotavapor at low pressure to give the solid product which was then crystallized with alcohol-chloroform (1:1 v/v) mixture to give the colourless crystals of title compound (yield 100%, m.p. 490-493 K). IR (KBr): ν_max 3556, 3500 (N-H), 3312 (OH), 3175, 1727, 1682, 1605, 1429, 1340, 1296, 1218, 1179, 1113, 933, 742, 659. IR spectrum was taken on Shimadzu IR-408 Perkin Elmer 1800 (FTIR). The melting point was taken on Thermo Fisher digital melting point apparatus of IA9000 series and is uncorrected.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of the title compound, viewed along the c axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

3a,8a-Dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-dione top

Crystal data top

C₁₀H₈N₂O₄	Z = 2
M_r = 220.18	F(000) = 228
Triclinic, P1	D_x = 1.598 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7914 (2) Å	Cell parameters from 2749 reflections
b = 7.3201 (2) Å	θ = 3.1–27.6°
c = 9.5006 (3) Å	µ = 0.13 mm⁻¹
α = 94.258 (1)°	T = 296 K
β = 102.773 (1)°	Plate, colourless
γ = 93.725 (1)°	0.39 × 0.15 × 0.05 mm
V = 457.74 (2) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2081 independent reflections
Radiation source: fine-focus sealed tube	1634 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.952, T_max = 0.994	k = −9→9
6684 measured reflections	l = −12→12

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0511P)² + 0.1396P] where P = (F_o² + 2F_c²)/3
2081 reflections	(Δ/σ)_max = 0.001
177 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₀H₈N₂O₄	γ = 93.725 (1)°
M_r = 220.18	V = 457.74 (2) Å³
Triclinic, P1	Z = 2
a = 6.7914 (2) Å	Mo Kα radiation
b = 7.3201 (2) Å	µ = 0.13 mm⁻¹
c = 9.5006 (3) Å	T = 296 K
α = 94.258 (1)°	0.39 × 0.15 × 0.05 mm
β = 102.773 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2081 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1634 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.994	R_int = 0.022
6684 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.25 e Å⁻³
2081 reflections	Δρ_min = −0.23 e Å⁻³
177 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	1.26218 (17)	0.50614 (16)	0.93570 (12)	0.0382 (3)
O2	0.73914 (19)	0.13075 (18)	0.94567 (13)	0.0394 (3)
O3	0.59082 (18)	0.39814 (17)	0.75936 (14)	0.0376 (3)
O4	0.8536 (2)	−0.15340 (16)	0.77260 (14)	0.0464 (4)
N1	0.9431 (2)	0.46753 (19)	0.78463 (15)	0.0345 (3)
N2	1.0569 (2)	0.23428 (18)	0.90164 (15)	0.0323 (3)
C1	1.1014 (2)	0.4122 (2)	0.87930 (16)	0.0294 (3)
C2	0.7722 (2)	0.3301 (2)	0.74365 (16)	0.0284 (3)
C3	0.7435 (2)	0.2416 (2)	0.59059 (16)	0.0279 (3)
C4	0.6895 (3)	0.3254 (3)	0.46259 (18)	0.0371 (4)
C5	0.6634 (3)	0.2169 (3)	0.33296 (19)	0.0431 (5)
C6	0.6904 (3)	0.0303 (3)	0.32948 (19)	0.0424 (4)
C7	0.7470 (3)	−0.0527 (2)	0.45616 (18)	0.0358 (4)
C8	0.7735 (2)	0.0553 (2)	0.58705 (17)	0.0290 (3)
C9	0.8272 (2)	−0.0003 (2)	0.73466 (17)	0.0303 (4)
C10	0.8466 (2)	0.1716 (2)	0.84121 (16)	0.0286 (3)
H4A	0.672 (3)	0.461 (3)	0.467 (2)	0.048 (5)*
H5A	0.617 (3)	0.274 (3)	0.245 (2)	0.056 (6)*
H6A	0.670 (3)	−0.043 (3)	0.237 (2)	0.059 (6)*
H7A	0.764 (3)	−0.183 (3)	0.455 (2)	0.048 (6)*
H1O3	0.605 (4)	0.440 (3)	0.852 (3)	0.070 (7)*
H1O2	0.735 (4)	0.242 (4)	1.002 (3)	0.089 (9)*
H1N2	1.128 (3)	0.188 (3)	0.970 (2)	0.041 (5)*
H1N1	0.935 (3)	0.580 (3)	0.765 (2)	0.049 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0395 (7)	0.0379 (7)	0.0335 (6)	−0.0069 (5)	0.0049 (5)	−0.0023 (5)
O2	0.0501 (8)	0.0369 (7)	0.0315 (6)	−0.0046 (5)	0.0115 (5)	0.0064 (5)
O3	0.0399 (7)	0.0384 (7)	0.0335 (7)	0.0137 (5)	0.0045 (5)	−0.0005 (5)
O4	0.0613 (9)	0.0239 (6)	0.0474 (8)	0.0061 (5)	−0.0038 (6)	0.0071 (5)
N1	0.0422 (8)	0.0218 (7)	0.0354 (8)	0.0001 (6)	−0.0006 (6)	0.0058 (6)
N2	0.0358 (8)	0.0279 (7)	0.0283 (7)	0.0019 (6)	−0.0040 (6)	0.0056 (5)
C1	0.0363 (8)	0.0285 (8)	0.0225 (7)	0.0006 (6)	0.0066 (6)	−0.0014 (6)
C2	0.0340 (8)	0.0225 (7)	0.0272 (8)	0.0045 (6)	0.0028 (6)	0.0037 (6)
C3	0.0291 (8)	0.0284 (8)	0.0257 (7)	0.0028 (6)	0.0040 (6)	0.0045 (6)
C4	0.0429 (10)	0.0378 (9)	0.0313 (9)	0.0058 (7)	0.0063 (7)	0.0108 (7)
C5	0.0442 (10)	0.0599 (12)	0.0259 (9)	0.0052 (9)	0.0068 (7)	0.0112 (8)
C6	0.0365 (10)	0.0602 (12)	0.0286 (9)	0.0014 (8)	0.0073 (7)	−0.0056 (8)
C7	0.0327 (9)	0.0353 (9)	0.0367 (9)	0.0032 (7)	0.0056 (7)	−0.0060 (7)
C8	0.0283 (8)	0.0277 (8)	0.0290 (8)	0.0018 (6)	0.0027 (6)	0.0021 (6)
C9	0.0317 (8)	0.0230 (7)	0.0329 (8)	0.0018 (6)	−0.0001 (6)	0.0036 (6)
C10	0.0341 (8)	0.0246 (7)	0.0250 (7)	0.0021 (6)	0.0015 (6)	0.0050 (6)

Geometric parameters (Å, º) top

O1—C1	1.2415 (18)	C2—C10	1.578 (2)
O2—C10	1.3939 (19)	C3—C4	1.390 (2)
O2—H1O2	0.94 (3)	C3—C8	1.391 (2)
O3—C2	1.392 (2)	C4—C5	1.385 (3)
O3—H1O3	0.89 (3)	C4—H4A	1.01 (2)
O4—C9	1.2145 (18)	C5—C6	1.388 (3)
N1—C1	1.346 (2)	C5—H5A	0.96 (2)
N1—C2	1.4496 (19)	C6—C7	1.378 (3)
N1—H1N1	0.86 (2)	C6—H6A	0.97 (2)
N2—C1	1.360 (2)	C7—C8	1.393 (2)
N2—C10	1.447 (2)	C7—H7A	0.96 (2)
N2—H1N2	0.83 (2)	C8—C9	1.464 (2)
C2—C3	1.513 (2)	C9—C10	1.535 (2)

C10—O2—H1O2	107.1 (16)	C3—C4—H4A	119.6 (11)
C2—O3—H1O3	108.0 (16)	C4—C5—C6	121.62 (16)
C1—N1—C2	113.31 (13)	C4—C5—H5A	117.3 (13)
C1—N1—H1N1	122.8 (14)	C6—C5—H5A	120.9 (13)
C2—N1—H1N1	122.7 (14)	C7—C6—C5	120.68 (17)
C1—N2—C10	112.65 (13)	C7—C6—H6A	119.2 (13)
C1—N2—H1N2	119.6 (13)	C5—C6—H6A	120.1 (13)
C10—N2—H1N2	122.8 (13)	C6—C7—C8	118.12 (17)
O1—C1—N1	126.05 (15)	C6—C7—H7A	121.2 (12)
O1—C1—N2	125.48 (15)	C8—C7—H7A	120.6 (12)
N1—C1—N2	108.47 (14)	C3—C8—C7	121.22 (15)
O3—C2—N1	112.93 (13)	C3—C8—C9	110.13 (14)
O3—C2—C3	108.64 (12)	C7—C8—C9	128.63 (15)
N1—C2—C3	113.22 (13)	O4—C9—C8	128.27 (15)
O3—C2—C10	115.83 (12)	O4—C9—C10	123.41 (14)
N1—C2—C10	102.17 (12)	C8—C9—C10	108.32 (12)
C3—C2—C10	103.71 (12)	O2—C10—N2	113.44 (12)
C4—C3—C8	120.46 (15)	O2—C10—C9	107.94 (12)
C4—C3—C2	127.23 (15)	N2—C10—C9	111.16 (13)
C8—C3—C2	112.30 (13)	O2—C10—C2	116.95 (13)
C5—C4—C3	117.90 (17)	N2—C10—C2	102.00 (11)
C5—C4—H4A	122.5 (11)	C9—C10—C2	104.99 (12)

C2—N1—C1—O1	−176.86 (15)	C6—C7—C8—C9	178.21 (15)
C2—N1—C1—N2	3.96 (19)	C3—C8—C9—O4	175.78 (16)
C10—N2—C1—O1	170.05 (15)	C7—C8—C9—O4	−2.4 (3)
C10—N2—C1—N1	−10.77 (19)	C3—C8—C9—C10	−4.17 (17)
C1—N1—C2—O3	128.62 (15)	C7—C8—C9—C10	177.62 (15)
C1—N1—C2—C3	−107.37 (15)	C1—N2—C10—O2	−114.40 (15)
C1—N1—C2—C10	3.51 (18)	C1—N2—C10—C9	123.74 (14)
O3—C2—C3—C4	60.0 (2)	C1—N2—C10—C2	12.28 (17)
N1—C2—C3—C4	−66.3 (2)	O4—C9—C10—O2	−47.5 (2)
C10—C2—C3—C4	−176.23 (15)	C8—C9—C10—O2	132.48 (13)
O3—C2—C3—C8	−118.71 (14)	O4—C9—C10—N2	77.5 (2)
N1—C2—C3—C8	114.97 (15)	C8—C9—C10—N2	−102.51 (14)
C10—C2—C3—C8	5.04 (17)	O4—C9—C10—C2	−172.92 (15)
C8—C3—C4—C5	1.1 (2)	C8—C9—C10—C2	7.03 (16)
C2—C3—C4—C5	−177.49 (16)	O3—C2—C10—O2	−7.76 (19)
C3—C4—C5—C6	−0.2 (3)	N1—C2—C10—O2	115.42 (14)
C4—C5—C6—C7	−0.8 (3)	C3—C2—C10—O2	−126.69 (13)
C5—C6—C7—C8	0.8 (3)	O3—C2—C10—N2	−132.12 (13)
C4—C3—C8—C7	−1.2 (2)	N1—C2—C10—N2	−8.94 (15)
C2—C3—C8—C7	177.66 (14)	C3—C2—C10—N2	108.95 (13)
C4—C3—C8—C9	−179.53 (14)	O3—C2—C10—C9	111.83 (14)
C2—C3—C8—C9	−0.71 (18)	N1—C2—C10—C9	−124.99 (13)
C6—C7—C8—C3	0.2 (2)	C3—C2—C10—C9	−7.09 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O1ⁱ	0.89 (3)	2.02 (3)	2.8653 (17)	158 (2)
O2—H1O2···O1ⁱ	0.95 (3)	1.89 (3)	2.8103 (17)	163 (2)
N2—H1N2···O4ⁱⁱ	0.83 (2)	2.454 (19)	3.1282 (19)	139.3 (18)
N1—H1N1···O4ⁱⁱⁱ	0.86 (2)	2.06 (2)	2.8841 (18)	159.4 (19)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₂O₄
M_r	220.18
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.7914 (2), 7.3201 (2), 9.5006 (3)
α, β, γ (°)	94.258 (1), 102.773 (1), 93.725 (1)
V (Å³)	457.74 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.39 × 0.15 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.952, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	6684, 2081, 1634
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.110, 1.05
No. of reflections	2081
No. of parameters	177
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.23

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O1ⁱ	0.89 (3)	2.02 (3)	2.8653 (17)	158 (2)
O2—H1O2···O1ⁱ	0.95 (3)	1.89 (3)	2.8103 (17)	163 (2)
N2—H1N2···O4ⁱⁱ	0.83 (2)	2.454 (19)	3.1282 (19)	139.3 (18)
N1—H1N1···O4ⁱⁱⁱ	0.86 (2)	2.06 (2)	2.8841 (18)	159.4 (19)

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

Footnotes

‡Thomson Reuters ResearcherID: A-5525-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and CKQ also thank USM for the Research University Grant (No. 1001/PFIZIK/811160).

References

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