2-(2-Hydroxy-ethyl)-3-[(2-hydroxy-ethyl)imino]isoindolin-1-one.

In the crystal structure of the title compound, C(12)H(14)N(2)O(3), mol-ecules are packed into layers parallel to (100). Each layer contains centrosymmetric dimers formed by a pair of strong O-H⋯N hydrogen bonds with an R(2) (2)(10) motif, while strong O-H⋯O hydrogen bonds forming C(10) chains connect mol-ecules into a two-dimensional network. Additional stabilization is supplied by weak C-H⋯O hydrogen bonds and weak π-π stacking inter-actions with centroid-centroid distances in the range 3.4220 (7)-3.9616 (7) Å.

Related literature

For background to the chemical and electrochemical properties of aromatic dicarbonyl compounds, see: Zuman (2004 ▶). For the use of reactions between phthalaldehyde and nucleophiles for the fluorimetric determination of amino acids, see: Roth (1971 ▶); For other structures isolated from systems in which kolamine was reacted with phthalaldehyde, see: Urban (2007a ▶, 2007b ▶). For hydrogen bonding and graph-set motifs, see: Desiraju & Steiner (1999 ▶); Etter et al. (1990 ▶). For the extinction correction, see: Becker & Coppens (1974 ▶).

Experimental

Crystal data

C12H14N2O3

M = 234.3

Orthorhombic,

a = 19.04539 (11) Å

b = 7.14668 (5) Å

c = 15.71068 (9) Å

V = 2138.40 (5) Å3

Z = 8

Cu Kα radiation

μ = 0.88 mm−1

T = 120 K

0.64 × 0.11 × 0.05 mm

Data collection

Oxford Diffraction Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005 ▶) T min = 0.547, T max = 0.916

40508 measured reflections

1829 independent reflections

1676 reflections with I > 3σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.088

S = 3.44

1829 reflections

161 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2005 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1997 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030487/lh2865sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030487/lh2865Isup2.hkl

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

C12H14N2O3	Dx = 1.455 Mg m−3
Mr = 234.3	Melting point = 373–375 K
Orthorhombic, Pccn	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 26197 reflections
a = 19.04539 (11) Å	θ = 2.8–65.3°
b = 7.14668 (5) Å	µ = 0.88 mm−1
c = 15.71068 (9) Å	T = 120 K
V = 2138.40 (5) Å3	Needle, brown
Z = 8	0.64 × 0.11 × 0.05 mm
F(000) = 992

Oxford Diffraction Gemini diffractometer	1829 independent reflections
Radiation source: Ultra (Cu) X-ray Source	1676 reflections with I > 3σ(I)
mirror	Rint = 0.032
Detector resolution: 10.3784 pixels mm-1	θmax = 65.4°, θmin = 2.8°
ω scans	h = −21→22
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005)	k = −7→8
Tmin = 0.547, Tmax = 0.916	l = −18→18
40508 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029	Hydrogen site location: difference Fourier map
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 3.44	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0004I2]
1829 reflections	(Δ/σ)max = 0.001
161 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.19 e Å−3
50 constraints	Extinction correction: B–C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 3600 (400)

	x	y	z	Uiso*/Ueq
O3	0.01643 (4)	0.37865 (12)	0.58348 (5)	0.0249 (3)
O2	0.02777 (4)	0.42770 (13)	0.19272 (5)	0.0254 (3)
N2	0.12251 (5)	0.53455 (13)	0.46306 (6)	0.0189 (3)
N1	0.17906 (5)	0.53362 (14)	0.33037 (6)	0.0195 (3)
O1	0.26033 (5)	0.52000 (13)	0.22084 (5)	0.0295 (3)
C8	0.17913 (6)	0.52397 (15)	0.41996 (7)	0.0167 (4)
C10	0.08334 (6)	0.38375 (17)	0.24969 (7)	0.0217 (3)
C3	0.25448 (7)	0.50383 (14)	0.44476 (7)	0.0168 (3)
C2	0.29391 (7)	0.50185 (15)	0.36982 (7)	0.0182 (4)
C6	0.40008 (7)	0.47776 (16)	0.44756 (8)	0.0228 (4)
C9	0.11818 (6)	0.56558 (17)	0.27593 (7)	0.0209 (4)
C4	0.28841 (6)	0.49167 (15)	0.52267 (8)	0.0202 (4)
C12	0.05695 (6)	0.54373 (18)	0.59873 (7)	0.0229 (4)
C11	0.12770 (6)	0.52705 (16)	0.55650 (7)	0.0198 (4)
C7	0.36643 (6)	0.49080 (15)	0.36957 (8)	0.0208 (4)
C5	0.36134 (7)	0.47820 (16)	0.52273 (8)	0.0228 (4)
C1	0.24599 (6)	0.51820 (16)	0.29654 (7)	0.0202 (4)
H1c10	0.117323	0.30469	0.22104	0.026*
H2c10	0.064404	0.321905	0.299633	0.026*
H1c9	0.132549	0.633958	0.225521	0.0251*
H2c9	0.084468	0.643488	0.305694	0.0251*
H1c12	0.063213	0.560506	0.659524	0.0275*
H2c12	0.032334	0.651588	0.576051	0.0275*
H1c11	0.158048	0.626955	0.576323	0.0238*
H2c11	0.149675	0.410391	0.573408	0.0238*
H1c6	0.448764	0.468686	0.44947	0.0273*
H1c4	0.263062	0.492517	0.573256	0.0243*
H1c7	0.391612	0.492081	0.318854	0.025*
H1c5	0.384849	0.469256	0.57446	0.0273*
H1o3	−0.0255 (9)	0.409 (2)	0.5715 (10)	0.0373*
H1o2	0.0205 (8)	0.335 (2)	0.1590 (10)	0.0381*

	U11	U22	U33	U12	U13	U23
O3	0.0162 (5)	0.0353 (5)	0.0231 (4)	0.0000 (4)	−0.0010 (3)	0.0066 (3)
O2	0.0200 (4)	0.0346 (5)	0.0217 (4)	0.0008 (4)	−0.0064 (3)	−0.0041 (4)
N2	0.0179 (5)	0.0237 (5)	0.0150 (5)	0.0000 (4)	0.0003 (4)	0.0005 (4)
N1	0.0172 (5)	0.0284 (6)	0.0128 (5)	0.0002 (4)	−0.0020 (4)	0.0000 (4)
O1	0.0266 (5)	0.0491 (6)	0.0130 (4)	0.0007 (4)	0.0017 (3)	−0.0006 (3)
C8	0.0195 (6)	0.0183 (6)	0.0123 (6)	−0.0009 (4)	−0.0015 (5)	0.0000 (4)
C10	0.0191 (6)	0.0295 (7)	0.0163 (6)	0.0012 (5)	−0.0023 (4)	0.0000 (4)
C3	0.0184 (6)	0.0168 (6)	0.0152 (6)	−0.0005 (4)	0.0009 (5)	−0.0003 (4)
C2	0.0201 (7)	0.0186 (6)	0.0159 (6)	0.0005 (4)	0.0000 (4)	−0.0010 (4)
C6	0.0179 (7)	0.0268 (7)	0.0235 (7)	0.0024 (5)	−0.0006 (5)	−0.0006 (5)
C9	0.0195 (6)	0.0293 (7)	0.0140 (6)	0.0014 (5)	−0.0030 (4)	0.0022 (5)
C4	0.0205 (7)	0.0242 (6)	0.0161 (6)	0.0005 (4)	0.0001 (5)	0.0005 (4)
C12	0.0221 (6)	0.0302 (7)	0.0163 (6)	0.0018 (5)	0.0012 (5)	0.0003 (4)
C11	0.0194 (6)	0.0264 (7)	0.0137 (6)	−0.0005 (4)	0.0001 (4)	0.0016 (4)
C7	0.0202 (7)	0.0228 (6)	0.0194 (7)	0.0013 (4)	0.0034 (5)	−0.0015 (4)
C5	0.0227 (7)	0.0271 (7)	0.0185 (6)	0.0009 (5)	−0.0036 (5)	0.0011 (4)
C1	0.0220 (6)	0.0243 (6)	0.0143 (6)	−0.0007 (5)	0.0003 (5)	−0.0010 (4)

O3—C12	1.4300 (15)	C4—C5	1.3923 (18)
O2—C10	1.4213 (13)	C12—C11	1.5067 (16)
N2—C8	1.2756 (15)	O3—H1o3	0.848 (17)
N2—C11	1.4724 (15)	O2—H1o2	0.859 (16)
N1—C8	1.4092 (15)	C10—H1c10	0.9700
N1—C9	1.4587 (14)	C10—H2c10	0.9700
N1—C1	1.3856 (15)	C6—H1c6	0.9300
O1—C1	1.2204 (14)	C9—H1c9	0.9700
C8—C3	1.4940 (17)	C9—H2c9	0.9700
C10—C9	1.5163 (17)	C4—H1c4	0.9300
C3—C2	1.3966 (16)	C12—H1c12	0.9700
C3—C4	1.3867 (17)	C12—H2c12	0.9700
C2—C7	1.3833 (17)	C11—H1c11	0.9700
C2—C1	1.4737 (16)	C11—H2c11	0.9700
C6—C7	1.3860 (17)	C7—H1c7	0.9300
C6—C5	1.3925 (17)	C5—H1c5	0.9300
C8—N2—C11	118.06 (10)	O2—C10—H2c10	109.47
C8—N1—C9	126.45 (9)	C9—C10—H1c10	109.47
C8—N1—C1	112.22 (9)	C9—C10—H2c10	109.47
C9—N1—C1	121.26 (9)	H1c10—C10—H2c10	110.98
N2—C8—N1	121.76 (10)	N1—C9—H1c9	109.47
N2—C8—C3	132.79 (10)	N1—C9—H2c9	109.47
N1—C8—C3	105.44 (9)	C10—C9—H1c9	109.47
O2—C10—C9	107.92 (9)	C10—C9—H2c9	109.47
C8—C3—C2	107.31 (10)	H1c9—C9—H2c9	106.93
C8—C3—C4	133.15 (11)	O3—C12—H1c12	109.47
C2—C3—C4	119.53 (11)	O3—C12—H2c12	109.47
C3—C2—C7	122.67 (11)	C11—C12—H1c12	109.47
C3—C2—C1	108.95 (10)	C11—C12—H2c12	109.47
C7—C2—C1	128.36 (11)	H1c12—C12—H2c12	108.84
C7—C6—C5	120.31 (12)	N2—C11—H1c11	109.47
N1—C9—C10	111.90 (10)	N2—C11—H2c11	109.47
C3—C4—C5	118.03 (11)	C12—C11—H1c11	109.47
O3—C12—C11	110.10 (9)	C12—C11—H2c11	109.47
N2—C11—C12	112.09 (9)	H1c11—C11—H2c11	106.72
C2—C7—C6	117.58 (11)	C3—C4—H1c4	120.79
C6—C5—C4	121.87 (11)	C5—C4—H1c4	121.18
N1—C1—O1	125.37 (11)	C6—C5—H1c5	119.07
N1—C1—C2	106.05 (9)	C4—C5—H1c5	119.06
O1—C1—C2	128.58 (11)	C7—C6—H1c6	119.61
C12—O3—H1o3	109.5 (10)	C5—C6—H1c6	120.07
C10—O2—H1o2	109.8 (10)	C2—C7—H1c7	121.12
O2—C10—H1c10	109.47	C6—C7—H1c7	121.30

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···N2i	0.849 (17)	1.968 (17)	2.8145 (12)	175.8 (16)
O2—H1O2···O3ii	0.860 (15)	1.935 (15)	2.7903 (12)	173.0 (15)
C9—H2C9···O3i	0.97	2.60	3.4074 (14)	141
C4—H1C4···O1iii	0.93	2.37	3.2553 (15)	159
C5—H1C5···O2iii	0.93	2.51	3.4239 (15)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯N2i	0.85 (2)	1.97 (2)	2.8145 (12)	176 (2)
O2—H1O2⋯O3ii	0.86 (2)	1.94 (2)	2.7903 (12)	173 (2)
C9—H2C9⋯O3i	0.97	2.60	3.4074 (14)	141
C4—H1C4⋯O1iii	0.93	2.37	3.2553 (15)	159
C5—H1C5⋯O2iii	0.93	2.51	3.4239 (15)	167

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