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In the title compound, C10H9NO4, the 2-oxo-3,4-dihydro-1,4-benzoxazine unit is not planar. Adjacent mol­ecules are linked together to form a two-dimensional supra­molecular structure through C—H...O and O—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702613X/xu2260sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680702613X/xu2260Isup2.hkl
Contains datablock I

CCDC reference: 654868

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.053
  • wR factor = 0.171
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT432_ALERT_2_C Short Inter X...Y Contact N1 .. C1 .. 3.04 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Crystal engineering has been widely applied in the design of functional materials and coordination polymers (Yagai, 2006). Because of the various types and a number of supramolecular architectures, hydrogen bonds are widely used in crystal engineering (Desiraju, 2003). Carboxylic acids have strong and directional hydrogen bonds so that they are greatly applied in crystal engineering (Desiraju, 1995). We now report one of carboxylic acids compound, which has two-dimensional network connected through intermolecular hydrogen bonding.

The crystal structure of title compound is shown in Fig. 1. The compound is made up of a benzene ring, a lactonic ring and a acetic acid, which bonds to the N atom of the lactonic ring. The planes of the benzene and lactonic ring are tilted at an angle of 171.4°.

In the crystal structure, the adjacent molecules are connected together to form one-dimensional chain along b axis through C2—H2B···O1ii and C4—H4B···O2ii [symmetry code: (ii) 0.5 - x,0.5 + y,-0.5 - z] interactions. The O4—H4···O3 intermolecular H-bonds link the adjacent molecules to form eight-membered rings (R22(8)), which join the adjacent chains together to form two-dimensional network (Fig.2).

Related literature top

For general background, see: Yagai (2006); Desiraju (1995). For a related structure, see: Desiraju (2003).

Experimental top

The o-amino-phenol (1.09 g, 10 mmol), monochloroacetic acid (1.89 g, 20 mmol) and anhydrous sodium carbonate (2.12 g, 20 mmol) were mixed in water (50 ml). The mixture was refluxed for 3 h and then was adjusted to pH = 1 with hydrochloric acid (6 mol/l). The resulting white precipitate was separeted and dissolved with ethanol. The ethanol solution was slowly evaporization at room temperature. The colourless crystals were obtained after one week.

Refinement top

All H atoms were placed geometrically and treated as riding on their parent atoms, with C—H = 0.93 (aromatic), 0.97 (methylene) and 0.82 Å (hydroxyl). The Uiso(H) values were set at 1.2Ueq(C) for all C-bound H atoms, 1.5Ueq(0) for O-bound H atoms.

Structure description top

Crystal engineering has been widely applied in the design of functional materials and coordination polymers (Yagai, 2006). Because of the various types and a number of supramolecular architectures, hydrogen bonds are widely used in crystal engineering (Desiraju, 2003). Carboxylic acids have strong and directional hydrogen bonds so that they are greatly applied in crystal engineering (Desiraju, 1995). We now report one of carboxylic acids compound, which has two-dimensional network connected through intermolecular hydrogen bonding.

The crystal structure of title compound is shown in Fig. 1. The compound is made up of a benzene ring, a lactonic ring and a acetic acid, which bonds to the N atom of the lactonic ring. The planes of the benzene and lactonic ring are tilted at an angle of 171.4°.

In the crystal structure, the adjacent molecules are connected together to form one-dimensional chain along b axis through C2—H2B···O1ii and C4—H4B···O2ii [symmetry code: (ii) 0.5 - x,0.5 + y,-0.5 - z] interactions. The O4—H4···O3 intermolecular H-bonds link the adjacent molecules to form eight-membered rings (R22(8)), which join the adjacent chains together to form two-dimensional network (Fig.2).

For general background, see: Yagai (2006); Desiraju (1995). For a related structure, see: Desiraju (2003).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).
[Figure 2] Fig. 2. The two-dimensional net formed by hydrogen-bonding [symmetry codes: (i) -x + 1, -y + 1, -z, (ii) 0.5 - x,0.5 + y,-0.5 - z].
2-Oxo-3,4-dihydro-1,4-benzoxazine-4-acetic acid top
Crystal data top
C10H9NO4F(000) = 864
Mr = 207.18Dx = 1.472 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 878 reflections
a = 21.782 (3) Åθ = 3.0–25.7°
b = 9.743 (2) ŵ = 0.12 mm1
c = 9.271 (2) ÅT = 298 K
β = 108.178 (2)°Block, colourless
V = 1869.2 (6) Å30.56 × 0.49 × 0.20 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
887 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.069
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
φ and ω scansh = 2325
4535 measured reflectionsk = 1111
1632 independent reflectionsl = 1011
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0793P)2]
where P = (Fo2 + 2Fc2)/3
1632 reflections(Δ/σ)max < 0.001
136 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C10H9NO4V = 1869.2 (6) Å3
Mr = 207.18Z = 8
Monoclinic, C2/cMo Kα radiation
a = 21.782 (3) ŵ = 0.12 mm1
b = 9.743 (2) ÅT = 298 K
c = 9.271 (2) Å0.56 × 0.49 × 0.20 mm
β = 108.178 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
887 reflections with I > 2σ(I)
4535 measured reflectionsRint = 0.069
1632 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.171H-atom parameters constrained
S = 1.00Δρmax = 0.27 e Å3
1632 reflectionsΔρmin = 0.24 e Å3
136 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.32873 (10)0.2976 (3)0.0161 (3)0.0388 (7)
O10.28240 (10)0.0464 (2)0.1180 (2)0.0483 (6)
O20.21904 (11)0.1524 (2)0.3167 (3)0.0583 (7)
O30.44418 (11)0.3817 (3)0.0316 (3)0.0690 (8)
O40.44513 (11)0.5747 (3)0.0959 (3)0.0738 (9)
H40.47890.58760.07620.111*
C10.26313 (15)0.1613 (4)0.2008 (4)0.0432 (8)
C20.29897 (14)0.2909 (4)0.1473 (3)0.0471 (9)
H2A0.33230.30090.19560.057*
H2B0.26940.36750.17930.057*
C30.42010 (15)0.4568 (4)0.0387 (4)0.0451 (9)
C40.35799 (13)0.4265 (3)0.0716 (3)0.0421 (8)
H4A0.36640.42920.18060.051*
H4B0.32730.49890.02750.051*
C50.35776 (13)0.1763 (3)0.0847 (3)0.0364 (8)
C60.33470 (13)0.0503 (4)0.0168 (3)0.0405 (8)
C70.35902 (16)0.0716 (4)0.0774 (4)0.0546 (10)
H70.34250.15280.02740.066*
C80.40803 (19)0.0760 (5)0.2126 (5)0.0639 (11)
H80.42570.15940.25410.077*
C90.43049 (17)0.0447 (5)0.2854 (4)0.0646 (12)
H90.46240.04230.37930.078*
C100.40682 (15)0.1697 (4)0.2226 (4)0.0515 (10)
H100.42390.25030.27300.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0322 (13)0.0429 (18)0.0430 (15)0.0036 (12)0.0140 (11)0.0002 (12)
O10.0438 (13)0.0383 (15)0.0635 (15)0.0034 (10)0.0179 (12)0.0015 (12)
O20.0514 (14)0.0624 (19)0.0551 (15)0.0046 (12)0.0081 (12)0.0097 (12)
O30.0620 (16)0.072 (2)0.091 (2)0.0323 (14)0.0506 (15)0.0346 (15)
O40.0589 (16)0.072 (2)0.103 (2)0.0343 (13)0.0433 (15)0.0387 (15)
C10.0378 (18)0.044 (2)0.051 (2)0.0023 (15)0.0188 (16)0.0058 (17)
C20.0428 (19)0.051 (2)0.046 (2)0.0036 (16)0.0106 (15)0.0031 (16)
C30.0396 (18)0.049 (2)0.0473 (19)0.0109 (16)0.0149 (16)0.0048 (17)
C40.0391 (17)0.040 (2)0.0482 (19)0.0076 (15)0.0158 (15)0.0048 (15)
C50.0312 (16)0.037 (2)0.0481 (19)0.0005 (14)0.0222 (14)0.0042 (15)
C60.0291 (16)0.048 (2)0.0487 (19)0.0018 (15)0.0191 (15)0.0051 (17)
C70.052 (2)0.046 (3)0.076 (3)0.0068 (17)0.035 (2)0.0116 (19)
C80.057 (2)0.064 (3)0.080 (3)0.020 (2)0.035 (2)0.027 (2)
C90.048 (2)0.094 (4)0.055 (2)0.021 (2)0.0195 (18)0.024 (2)
C100.0415 (19)0.061 (3)0.054 (2)0.0002 (17)0.0173 (17)0.0057 (18)
Geometric parameters (Å, º) top
N1—C51.397 (4)C4—H4A0.9700
N1—C41.429 (4)C4—H4B0.9700
N1—C21.451 (4)C5—C101.389 (4)
O1—C11.348 (4)C5—C61.399 (4)
O1—C61.404 (3)C6—C71.350 (5)
O2—C11.200 (3)C7—C81.370 (5)
O3—C31.204 (4)C7—H70.9300
O4—C31.310 (4)C8—C91.368 (6)
O4—H40.8200C8—H80.9300
C1—C21.486 (4)C9—C101.379 (5)
C2—H2A0.9700C9—H90.9300
C2—H2B0.9700C10—H100.9300
C3—C41.506 (4)
C5—N1—C4119.5 (2)C3—C4—H4B108.4
C5—N1—C2115.3 (3)H4A—C4—H4B107.5
C4—N1—C2114.8 (3)C10—C5—N1124.5 (3)
C1—O1—C6120.4 (3)C10—C5—C6116.0 (3)
C3—O4—H4109.5N1—C5—C6119.3 (3)
O2—C1—O1118.0 (3)C7—C6—C5123.1 (3)
O2—C1—C2123.4 (3)C7—C6—O1116.8 (3)
O1—C1—C2118.5 (3)C5—C6—O1120.1 (3)
N1—C2—C1113.8 (3)C6—C7—C8120.0 (4)
N1—C2—H2A108.8C6—C7—H7120.0
C1—C2—H2A108.8C8—C7—H7120.0
N1—C2—H2B108.8C9—C8—C7118.8 (4)
C1—C2—H2B108.8C9—C8—H8120.6
H2A—C2—H2B107.7C7—C8—H8120.6
O3—C3—O4123.7 (3)C8—C9—C10121.5 (4)
O3—C3—C4124.1 (3)C8—C9—H9119.3
O4—C3—C4112.1 (3)C10—C9—H9119.3
N1—C4—C3115.3 (3)C9—C10—C5120.5 (4)
N1—C4—H4A108.4C9—C10—H10119.7
C3—C4—H4A108.4C5—C10—H10119.7
N1—C4—H4B108.4
C6—O1—C1—O2178.5 (2)C10—C5—C6—C71.7 (4)
C6—O1—C1—C20.8 (4)N1—C5—C6—C7178.4 (3)
C5—N1—C2—C141.0 (3)C10—C5—C6—O1176.0 (2)
C4—N1—C2—C1174.1 (2)N1—C5—C6—O10.7 (4)
O2—C1—C2—N1154.2 (3)C1—O1—C6—C7167.6 (3)
O1—C1—C2—N128.2 (4)C1—O1—C6—C514.6 (4)
C5—N1—C4—C370.7 (3)C5—C6—C7—C80.9 (5)
C2—N1—C4—C372.7 (3)O1—C6—C7—C8176.9 (3)
O3—C3—C4—N11.5 (5)C6—C7—C8—C91.4 (5)
O4—C3—C4—N1178.4 (3)C7—C8—C9—C102.8 (5)
C4—N1—C5—C1013.0 (4)C8—C9—C10—C51.9 (5)
C2—N1—C5—C10156.2 (3)N1—C5—C10—C9176.8 (3)
C4—N1—C5—C6170.6 (2)C6—C5—C10—C90.3 (4)
C2—N1—C5—C627.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O3i0.821.872.692 (3)180
C2—H2B···O1ii0.972.553.416 (4)148
C4—H4B···O2ii0.972.423.282 (4)148
Symmetry codes: (i) x+1, y+1, z; (ii) x+1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC10H9NO4
Mr207.18
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)21.782 (3), 9.743 (2), 9.271 (2)
β (°) 108.178 (2)
V3)1869.2 (6)
Z8
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.56 × 0.49 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4535, 1632, 887
Rint0.069
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.171, 1.00
No. of reflections1632
No. of parameters136
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.24

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O3i0.821.872.692 (3)180
C2—H2B···O1ii0.972.553.416 (4)148
C4—H4B···O2ii0.972.423.282 (4)148
Symmetry codes: (i) x+1, y+1, z; (ii) x+1/2, y+1/2, z1/2.
 

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