Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047113/cs2054sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047113/cs2054Isup2.hkl |
CCDC reference: 663853
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.126
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C2 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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 compound was obtained by acidic hydrolysis of ortho-nitro-benzaldehyde cyanohydrin according to a known procedure (Heller, 1904). Crystals suitable for X-ray analysis were obtained by recrystallization of the crude reaction product from boiling water.
All H atoms were located in a difference map and refined as riding on their parent atoms. One common isotropic displacement parameter for all H atoms was refined to Uiso(H) = 0.041 (2).
Racemic 2-hydroxy-2-ortho-nitrophenyl acetic acid (I) acid was prepared as a chelating molecule bearing the sterically demanding ortho-nitro-phenyl group. In the molecular structure, the best planes of the nitro function and the aromatic ring enclose a tilt angle of 31.2 (2)°. The molecules of (I) are stiffened by intramolecular hydrogen bonds (Fig. 1). The 2-hydroxy function is a hydrogen-bond donor towards – listed in descending order of the bond's stabilities in terms of both the H—A distances and the D—H—A angles – a nitro-O atom in an intermolecular contact, the double-bonded O atom of the carboxylic group, and another nitro-O atom. The latter two contacts in the thus trifurcated bond are intramolecular.
In the crystal structure of (I), each molecule is part of a hydrogen-bonded ribbon and thus has two hydrogen-bonded neighbours. Each individual molecular contact comprises two bonds in a centrosymmetric pattern: the first pattern resembles the common motif of carboxylic-acid dimers (pink hydrogen bonds in Fig. 2); in the second pattern, hydroxy and nitro functions are connected in a similar way (green bonds in Fig. 2). The three-dimensional structure is formed by hydrophobic interaction of the phenyl groups which enclose the ribbons laterally (Fig. 2).
The compound was prepared according to a known procedure (Heller, 1904).
Data collection: COLLECT (Nonius, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C8H7NO5 | F(000) = 408 |
Mr = 197.15 | Dx = 1.601 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 13027 reflections |
a = 9.4343 (3) Å | θ = 3.1–27.5° |
b = 9.7690 (5) Å | µ = 0.14 mm−1 |
c = 9.8842 (5) Å | T = 200 K |
β = 116.130 (2)° | Block, yellow |
V = 817.86 (6) Å3 | 0.14 × 0.10 × 0.08 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 1466 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 27.5°, θmin = 3.2° |
φ/ω scans | h = −12→12 |
3617 measured reflections | k = −12→12 |
1871 independent reflections | l = −12→12 |
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)] = 0.046 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.126 | Only H-atom displacement parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0596P)2 + 0.4137P] where P = (Fo2 + 2Fc2)/3 |
1871 reflections | (Δ/σ)max < 0.001 |
128 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C8H7NO5 | V = 817.86 (6) Å3 |
Mr = 197.15 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.4343 (3) Å | µ = 0.14 mm−1 |
b = 9.7690 (5) Å | T = 200 K |
c = 9.8842 (5) Å | 0.14 × 0.10 × 0.08 mm |
β = 116.130 (2)° |
Nonius KappaCCD diffractometer | 1466 reflections with I > 2σ(I) |
3617 measured reflections | Rint = 0.020 |
1871 independent reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.126 | Only H-atom displacement parameters refined |
S = 1.04 | Δρmax = 0.50 e Å−3 |
1871 reflections | Δρmin = −0.25 e Å−3 |
128 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. |
x | y | z | Uiso*/Ueq | ||
O3 | 0.99600 (16) | 0.23800 (15) | 0.14149 (16) | 0.0418 (4) | |
H83 | 1.0642 | 0.1602 | 0.1755 | 0.041 (2)* | |
O2 | 0.82437 (14) | 0.08167 (15) | 0.36283 (14) | 0.0402 (4) | |
H82 | 0.8597 | 0.0329 | 0.4448 | 0.041 (2)* | |
O1 | 1.07440 (14) | 0.07928 (14) | 0.39310 (14) | 0.0378 (3) | |
O4 | 0.76077 (16) | −0.05081 (16) | −0.15598 (15) | 0.0456 (4) | |
O5 | 0.89088 (15) | −0.03814 (15) | 0.08572 (14) | 0.0408 (4) | |
N | 0.78192 (16) | −0.00364 (15) | −0.03350 (16) | 0.0298 (3) | |
C1 | 0.9378 (2) | 0.1182 (2) | 0.32753 (19) | 0.0327 (4) | |
C2 | 0.8853 (2) | 0.2223 (2) | 0.2006 (2) | 0.0334 (4) | |
H2 | 0.8834 | 0.3123 | 0.2481 | 0.041 (2)* | |
C3 | 0.7177 (2) | 0.20068 (19) | 0.07818 (19) | 0.0302 (4) | |
C4 | 0.66966 (19) | 0.09861 (18) | −0.03184 (18) | 0.0281 (4) | |
C5 | 0.5157 (2) | 0.08671 (19) | −0.14383 (19) | 0.0323 (4) | |
H5 | 0.4882 | 0.0162 | −0.2173 | 0.041 (2)* | |
C6 | 0.4034 (2) | 0.1789 (2) | −0.1468 (2) | 0.0375 (4) | |
H6 | 0.2972 | 0.1717 | −0.2216 | 0.041 (2)* | |
C7 | 0.4467 (2) | 0.2817 (2) | −0.0402 (2) | 0.0423 (5) | |
H7 | 0.3699 | 0.3455 | −0.0419 | 0.041 (2)* | |
C8 | 0.6010 (2) | 0.2925 (2) | 0.0689 (2) | 0.0382 (4) | |
H8 | 0.6283 | 0.3650 | 0.1400 | 0.041 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3 | 0.0355 (7) | 0.0453 (8) | 0.0493 (8) | 0.0044 (6) | 0.0229 (7) | 0.0084 (6) |
O2 | 0.0289 (7) | 0.0636 (9) | 0.0260 (7) | 0.0005 (6) | 0.0101 (5) | 0.0037 (6) |
O1 | 0.0264 (6) | 0.0541 (8) | 0.0300 (7) | 0.0014 (6) | 0.0096 (5) | 0.0017 (6) |
O4 | 0.0412 (8) | 0.0571 (9) | 0.0332 (7) | 0.0082 (6) | 0.0117 (6) | −0.0134 (6) |
O5 | 0.0384 (7) | 0.0454 (8) | 0.0307 (7) | 0.0119 (6) | 0.0079 (6) | 0.0031 (6) |
N | 0.0275 (7) | 0.0326 (8) | 0.0277 (8) | −0.0007 (6) | 0.0108 (6) | −0.0009 (6) |
C1 | 0.0284 (9) | 0.0438 (10) | 0.0245 (8) | −0.0032 (8) | 0.0104 (7) | −0.0069 (7) |
C2 | 0.0283 (9) | 0.0373 (10) | 0.0336 (9) | 0.0001 (7) | 0.0128 (8) | −0.0044 (7) |
C3 | 0.0287 (8) | 0.0358 (9) | 0.0258 (8) | 0.0027 (7) | 0.0118 (7) | 0.0032 (7) |
C4 | 0.0279 (8) | 0.0325 (9) | 0.0256 (8) | 0.0019 (7) | 0.0132 (7) | 0.0030 (7) |
C5 | 0.0289 (9) | 0.0393 (10) | 0.0261 (9) | −0.0010 (7) | 0.0097 (7) | 0.0045 (7) |
C6 | 0.0270 (9) | 0.0491 (11) | 0.0331 (10) | 0.0052 (8) | 0.0101 (7) | 0.0102 (8) |
C7 | 0.0353 (10) | 0.0507 (12) | 0.0422 (11) | 0.0148 (9) | 0.0182 (9) | 0.0086 (9) |
C8 | 0.0395 (10) | 0.0422 (11) | 0.0331 (10) | 0.0079 (8) | 0.0161 (8) | −0.0006 (8) |
O3—C2 | 1.412 (2) | C3—C8 | 1.391 (3) |
O3—H83 | 0.9560 | C3—C4 | 1.396 (2) |
O2—C1 | 1.313 (2) | C4—C5 | 1.390 (2) |
O2—H82 | 0.8701 | C5—C6 | 1.381 (3) |
O1—C1 | 1.220 (2) | C5—H5 | 0.9500 |
O4—N | 1.2269 (19) | C6—C7 | 1.381 (3) |
O5—N | 1.2214 (18) | C6—H6 | 0.9500 |
N—C4 | 1.461 (2) | C7—C8 | 1.382 (3) |
C1—C2 | 1.518 (3) | C7—H7 | 0.9500 |
C2—C3 | 1.524 (2) | C8—H8 | 0.9500 |
C2—H2 | 1.0000 | ||
C2—O3—H83 | 105.9 | C4—C3—C2 | 125.80 (15) |
C1—O2—H82 | 111.9 | C5—C4—C3 | 123.17 (16) |
O5—N—O4 | 123.39 (15) | C5—C4—N | 116.24 (15) |
O5—N—C4 | 118.95 (14) | C3—C4—N | 120.59 (14) |
O4—N—C4 | 117.66 (14) | C6—C5—C4 | 119.02 (17) |
O1—C1—O2 | 124.62 (18) | C6—C5—H5 | 120.5 |
O1—C1—C2 | 122.08 (16) | C4—C5—H5 | 120.5 |
O2—C1—C2 | 113.20 (15) | C7—C6—C5 | 119.45 (17) |
O3—C2—C1 | 112.52 (14) | C7—C6—H6 | 120.3 |
O3—C2—C3 | 112.57 (14) | C5—C6—H6 | 120.3 |
C1—C2—C3 | 114.21 (15) | C6—C7—C8 | 120.45 (18) |
O3—C2—H2 | 105.5 | C6—C7—H7 | 119.8 |
C1—C2—H2 | 105.5 | C8—C7—H7 | 119.8 |
C3—C2—H2 | 105.5 | C7—C8—C3 | 122.22 (18) |
C8—C3—C4 | 115.67 (16) | C7—C8—H8 | 118.9 |
C8—C3—C2 | 118.48 (16) | C3—C8—H8 | 118.9 |
O1—C1—C2—O3 | 16.5 (2) | O5—N—C4—C5 | −148.82 (16) |
O2—C1—C2—O3 | −166.89 (15) | O4—N—C4—C5 | 30.9 (2) |
O1—C1—C2—C3 | 146.46 (17) | O5—N—C4—C3 | 30.7 (2) |
O2—C1—C2—C3 | −37.0 (2) | O4—N—C4—C3 | −149.49 (17) |
O3—C2—C3—C8 | −121.79 (18) | C3—C4—C5—C6 | −0.6 (3) |
C1—C2—C3—C8 | 108.29 (19) | N—C4—C5—C6 | 178.92 (15) |
O3—C2—C3—C4 | 55.5 (2) | C4—C5—C6—C7 | 0.9 (3) |
C1—C2—C3—C4 | −74.4 (2) | C5—C6—C7—C8 | −0.1 (3) |
C8—C3—C4—C5 | −0.5 (3) | C6—C7—C8—C3 | −1.1 (3) |
C2—C3—C4—C5 | −177.85 (17) | C4—C3—C8—C7 | 1.3 (3) |
C8—C3—C4—N | 180.00 (16) | C2—C3—C8—C7 | 178.90 (17) |
C2—C3—C4—N | 2.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H82···O1i | 0.87 | 1.81 | 2.679 (2) | 176 |
O3—H83···O4ii | 0.96 | 2.05 | 2.888 (2) | 146 |
O3—H83···O1 | 0.96 | 2.25 | 2.742 (2) | 111 |
O3—H83···O5 | 0.96 | 2.44 | 2.843 (2) | 105 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+2, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C8H7NO5 |
Mr | 197.15 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 200 |
a, b, c (Å) | 9.4343 (3), 9.7690 (5), 9.8842 (5) |
β (°) | 116.130 (2) |
V (Å3) | 817.86 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.14 |
Crystal size (mm) | 0.14 × 0.10 × 0.08 |
Data collection | |
Diffractometer | Nonius KappaCCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3617, 1871, 1466 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.126, 1.04 |
No. of reflections | 1871 |
No. of parameters | 128 |
H-atom treatment | Only H-atom displacement parameters refined |
Δρmax, Δρmin (e Å−3) | 0.50, −0.25 |
Computer programs: COLLECT (Nonius, 2004), SCALEPACK (Otwinowski & Minor, 1997), SCALEPACK and DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H82···O1i | 0.87 | 1.81 | 2.679 (2) | 176 |
O3—H83···O4ii | 0.96 | 2.05 | 2.888 (2) | 146 |
O3—H83···O1 | 0.96 | 2.25 | 2.742 (2) | 111 |
O3—H83···O5 | 0.96 | 2.44 | 2.843 (2) | 105 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+2, −y, −z. |
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Racemic 2-hydroxy-2-ortho-nitrophenyl acetic acid (I) acid was prepared as a chelating molecule bearing the sterically demanding ortho-nitro-phenyl group. In the molecular structure, the best planes of the nitro function and the aromatic ring enclose a tilt angle of 31.2 (2)°. The molecules of (I) are stiffened by intramolecular hydrogen bonds (Fig. 1). The 2-hydroxy function is a hydrogen-bond donor towards – listed in descending order of the bond's stabilities in terms of both the H—A distances and the D—H—A angles – a nitro-O atom in an intermolecular contact, the double-bonded O atom of the carboxylic group, and another nitro-O atom. The latter two contacts in the thus trifurcated bond are intramolecular.
In the crystal structure of (I), each molecule is part of a hydrogen-bonded ribbon and thus has two hydrogen-bonded neighbours. Each individual molecular contact comprises two bonds in a centrosymmetric pattern: the first pattern resembles the common motif of carboxylic-acid dimers (pink hydrogen bonds in Fig. 2); in the second pattern, hydroxy and nitro functions are connected in a similar way (green bonds in Fig. 2). The three-dimensional structure is formed by hydrophobic interaction of the phenyl groups which enclose the ribbons laterally (Fig. 2).