Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702613X/xu2260sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680702613X/xu2260Isup2.hkl |
CCDC reference: 654868
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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.
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.
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).
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.
C10H9NO4 | F(000) = 864 |
Mr = 207.18 | Dx = 1.472 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 878 reflections |
a = 21.782 (3) Å | θ = 3.0–25.7° |
b = 9.743 (2) Å | µ = 0.12 mm−1 |
c = 9.271 (2) Å | T = 298 K |
β = 108.178 (2)° | Block, colourless |
V = 1869.2 (6) Å3 | 0.56 × 0.49 × 0.20 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 887 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.069 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
φ and ω scans | h = −23→25 |
4535 measured reflections | k = −11→11 |
1632 independent reflections | l = −10→11 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.171 | H-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 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C10H9NO4 | V = 1869.2 (6) Å3 |
Mr = 207.18 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 21.782 (3) Å | µ = 0.12 mm−1 |
b = 9.743 (2) Å | T = 298 K |
c = 9.271 (2) Å | 0.56 × 0.49 × 0.20 mm |
β = 108.178 (2)° |
Bruker SMART CCD area-detector diffractometer | 887 reflections with I > 2σ(I) |
4535 measured reflections | Rint = 0.069 |
1632 independent reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.171 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.27 e Å−3 |
1632 reflections | Δρmin = −0.24 e Å−3 |
136 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.32873 (10) | 0.2976 (3) | 0.0161 (3) | 0.0388 (7) | |
O1 | 0.28240 (10) | 0.0464 (2) | −0.1180 (2) | 0.0483 (6) | |
O2 | 0.21904 (11) | 0.1524 (2) | −0.3167 (3) | 0.0583 (7) | |
O3 | 0.44418 (11) | 0.3817 (3) | −0.0316 (3) | 0.0690 (8) | |
O4 | 0.44513 (11) | 0.5747 (3) | 0.0959 (3) | 0.0738 (9) | |
H4 | 0.4789 | 0.5876 | 0.0762 | 0.111* | |
C1 | 0.26313 (15) | 0.1613 (4) | −0.2008 (4) | 0.0432 (8) | |
C2 | 0.29897 (14) | 0.2909 (4) | −0.1473 (3) | 0.0471 (9) | |
H2A | 0.3323 | 0.3009 | −0.1956 | 0.057* | |
H2B | 0.2694 | 0.3675 | −0.1793 | 0.057* | |
C3 | 0.42010 (15) | 0.4568 (4) | 0.0387 (4) | 0.0451 (9) | |
C4 | 0.35799 (13) | 0.4265 (3) | 0.0716 (3) | 0.0421 (8) | |
H4A | 0.3664 | 0.4292 | 0.1806 | 0.051* | |
H4B | 0.3273 | 0.4989 | 0.0275 | 0.051* | |
C5 | 0.35776 (13) | 0.1763 (3) | 0.0847 (3) | 0.0364 (8) | |
C6 | 0.33470 (13) | 0.0503 (4) | 0.0168 (3) | 0.0405 (8) | |
C7 | 0.35902 (16) | −0.0716 (4) | 0.0774 (4) | 0.0546 (10) | |
H7 | 0.3425 | −0.1528 | 0.0274 | 0.066* | |
C8 | 0.40803 (19) | −0.0760 (5) | 0.2126 (5) | 0.0639 (11) | |
H8 | 0.4257 | −0.1594 | 0.2541 | 0.077* | |
C9 | 0.43049 (17) | 0.0447 (5) | 0.2854 (4) | 0.0646 (12) | |
H9 | 0.4624 | 0.0423 | 0.3793 | 0.078* | |
C10 | 0.40682 (15) | 0.1697 (4) | 0.2226 (4) | 0.0515 (10) | |
H10 | 0.4239 | 0.2503 | 0.2730 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0322 (13) | 0.0429 (18) | 0.0430 (15) | −0.0036 (12) | 0.0140 (11) | −0.0002 (12) |
O1 | 0.0438 (13) | 0.0383 (15) | 0.0635 (15) | −0.0034 (10) | 0.0179 (12) | −0.0015 (12) |
O2 | 0.0514 (14) | 0.0624 (19) | 0.0551 (15) | −0.0046 (12) | 0.0081 (12) | −0.0097 (12) |
O3 | 0.0620 (16) | 0.072 (2) | 0.091 (2) | −0.0323 (14) | 0.0506 (15) | −0.0346 (15) |
O4 | 0.0589 (16) | 0.072 (2) | 0.103 (2) | −0.0343 (13) | 0.0433 (15) | −0.0387 (15) |
C1 | 0.0378 (18) | 0.044 (2) | 0.051 (2) | 0.0023 (15) | 0.0188 (16) | −0.0058 (17) |
C2 | 0.0428 (19) | 0.051 (2) | 0.046 (2) | −0.0036 (16) | 0.0106 (15) | 0.0031 (16) |
C3 | 0.0396 (18) | 0.049 (2) | 0.0473 (19) | −0.0109 (16) | 0.0149 (16) | −0.0048 (17) |
C4 | 0.0391 (17) | 0.040 (2) | 0.0482 (19) | −0.0076 (15) | 0.0158 (15) | −0.0048 (15) |
C5 | 0.0312 (16) | 0.037 (2) | 0.0481 (19) | 0.0005 (14) | 0.0222 (14) | 0.0042 (15) |
C6 | 0.0291 (16) | 0.048 (2) | 0.0487 (19) | 0.0018 (15) | 0.0191 (15) | 0.0051 (17) |
C7 | 0.052 (2) | 0.046 (3) | 0.076 (3) | 0.0068 (17) | 0.035 (2) | 0.0116 (19) |
C8 | 0.057 (2) | 0.064 (3) | 0.080 (3) | 0.020 (2) | 0.035 (2) | 0.027 (2) |
C9 | 0.048 (2) | 0.094 (4) | 0.055 (2) | 0.021 (2) | 0.0195 (18) | 0.024 (2) |
C10 | 0.0415 (19) | 0.061 (3) | 0.054 (2) | −0.0002 (17) | 0.0173 (17) | 0.0057 (18) |
N1—C5 | 1.397 (4) | C4—H4A | 0.9700 |
N1—C4 | 1.429 (4) | C4—H4B | 0.9700 |
N1—C2 | 1.451 (4) | C5—C10 | 1.389 (4) |
O1—C1 | 1.348 (4) | C5—C6 | 1.399 (4) |
O1—C6 | 1.404 (3) | C6—C7 | 1.350 (5) |
O2—C1 | 1.200 (3) | C7—C8 | 1.370 (5) |
O3—C3 | 1.204 (4) | C7—H7 | 0.9300 |
O4—C3 | 1.310 (4) | C8—C9 | 1.368 (6) |
O4—H4 | 0.8200 | C8—H8 | 0.9300 |
C1—C2 | 1.486 (4) | C9—C10 | 1.379 (5) |
C2—H2A | 0.9700 | C9—H9 | 0.9300 |
C2—H2B | 0.9700 | C10—H10 | 0.9300 |
C3—C4 | 1.506 (4) | ||
C5—N1—C4 | 119.5 (2) | C3—C4—H4B | 108.4 |
C5—N1—C2 | 115.3 (3) | H4A—C4—H4B | 107.5 |
C4—N1—C2 | 114.8 (3) | C10—C5—N1 | 124.5 (3) |
C1—O1—C6 | 120.4 (3) | C10—C5—C6 | 116.0 (3) |
C3—O4—H4 | 109.5 | N1—C5—C6 | 119.3 (3) |
O2—C1—O1 | 118.0 (3) | C7—C6—C5 | 123.1 (3) |
O2—C1—C2 | 123.4 (3) | C7—C6—O1 | 116.8 (3) |
O1—C1—C2 | 118.5 (3) | C5—C6—O1 | 120.1 (3) |
N1—C2—C1 | 113.8 (3) | C6—C7—C8 | 120.0 (4) |
N1—C2—H2A | 108.8 | C6—C7—H7 | 120.0 |
C1—C2—H2A | 108.8 | C8—C7—H7 | 120.0 |
N1—C2—H2B | 108.8 | C9—C8—C7 | 118.8 (4) |
C1—C2—H2B | 108.8 | C9—C8—H8 | 120.6 |
H2A—C2—H2B | 107.7 | C7—C8—H8 | 120.6 |
O3—C3—O4 | 123.7 (3) | C8—C9—C10 | 121.5 (4) |
O3—C3—C4 | 124.1 (3) | C8—C9—H9 | 119.3 |
O4—C3—C4 | 112.1 (3) | C10—C9—H9 | 119.3 |
N1—C4—C3 | 115.3 (3) | C9—C10—C5 | 120.5 (4) |
N1—C4—H4A | 108.4 | C9—C10—H10 | 119.7 |
C3—C4—H4A | 108.4 | C5—C10—H10 | 119.7 |
N1—C4—H4B | 108.4 | ||
C6—O1—C1—O2 | 178.5 (2) | C10—C5—C6—C7 | −1.7 (4) |
C6—O1—C1—C2 | 0.8 (4) | N1—C5—C6—C7 | −178.4 (3) |
C5—N1—C2—C1 | 41.0 (3) | C10—C5—C6—O1 | 176.0 (2) |
C4—N1—C2—C1 | −174.1 (2) | N1—C5—C6—O1 | −0.7 (4) |
O2—C1—C2—N1 | 154.2 (3) | C1—O1—C6—C7 | −167.6 (3) |
O1—C1—C2—N1 | −28.2 (4) | C1—O1—C6—C5 | 14.6 (4) |
C5—N1—C4—C3 | 70.7 (3) | C5—C6—C7—C8 | 0.9 (5) |
C2—N1—C4—C3 | −72.7 (3) | O1—C6—C7—C8 | −176.9 (3) |
O3—C3—C4—N1 | 1.5 (5) | C6—C7—C8—C9 | 1.4 (5) |
O4—C3—C4—N1 | −178.4 (3) | C7—C8—C9—C10 | −2.8 (5) |
C4—N1—C5—C10 | 13.0 (4) | C8—C9—C10—C5 | 1.9 (5) |
C2—N1—C5—C10 | 156.2 (3) | N1—C5—C10—C9 | 176.8 (3) |
C4—N1—C5—C6 | −170.6 (2) | C6—C5—C10—C9 | 0.3 (4) |
C2—N1—C5—C6 | −27.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O3i | 0.82 | 1.87 | 2.692 (3) | 180 |
C2—H2B···O1ii | 0.97 | 2.55 | 3.416 (4) | 148 |
C4—H4B···O2ii | 0.97 | 2.42 | 3.282 (4) | 148 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1/2, y+1/2, −z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C10H9NO4 |
Mr | 207.18 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 21.782 (3), 9.743 (2), 9.271 (2) |
β (°) | 108.178 (2) |
V (Å3) | 1869.2 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.56 × 0.49 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4535, 1632, 887 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.171, 1.00 |
No. of reflections | 1632 |
No. of parameters | 136 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.24 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O3i | 0.82 | 1.87 | 2.692 (3) | 180 |
C2—H2B···O1ii | 0.97 | 2.55 | 3.416 (4) | 148 |
C4—H4B···O2ii | 0.97 | 2.42 | 3.282 (4) | 148 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1/2, y+1/2, −z−1/2. |
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).