Retracted: 2-(1-Hydr­oxy-2-pyrid­yl)acetamide monohydrate

In the crystal structure of the title complex, C₇H₇N₂O₂·H₂O, inter­molecular O—H...O and N—H...O hydrogen bonds result in the formation of a supra­molecular network structure; intra­molecular O—H...O and O—H...N hydrogen bonds are also present.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.055
• wR factor = 0.187
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C5     -   C6      ..      17.45 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C6     -   C7      ..       7.39 su
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1A    ..  H3B     ..       1.13 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H1A    ..  O1      ..       3.10 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       2.63 Sigma
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.64 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.70
PLAT320_ALERT_2_C Check Hybridisation of  C6     in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C5     -   C6     ...       1.37 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3     ..  C6      ..       2.98 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3A    ..  O1      ..       2.61 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for O1     ..  O1      ..      91.00 Deg.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          7

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

In the synthesis of crystal structures by design, the assembly of molecular units in predefined arrangements is a key goal (Desiraju, 1995, 1997; Braga et al., 1998). Due to hydrogen-bonding interactions are of critical importance in biological systems, organic materials and coordination chemistry, hydrogen-bonding is currently the best tool in achieving this goal (Zaworotko, 1997; Braga & Grepioni, 2000). Supramolecular architectures are of considerable contemporary interest by virtue of their potential applications in various fields (Moulton & Zaworotko, 2001; Pan et al., 2001; Ma et al., 2001; Prior & Rosseinsky, 2001). We originally attempted to synthesize complexes featuring La metal chains by reaction of the lanthanum(III) ion with 1-hydroxy-2-acetylamido- pyridine ligand. Unfortunately, we obtained only the title compound, (I), and we report herein its crystal structure.

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). It contains one (C₇H₇N₂O₂) molecule and one water molecule.

In the crystal structure, intramolecular O—H···O and O—H···N and intermolecular O—H···O and N—H···O hydrogen bonds (Table 1) result in the formation of a supramolecular network structure (Fig. 2).

Related literature

For general background, see: Desiraju (1995, 1997); Braga et al. (1998); Zaworotko (1997); Braga & Grepioni (2000); Moulton & Zaworotko (2001); Pan et al. (2001); Ma et al. (2001); Prior & Rosseinsky (2001). For bond-length data, see: Allen et al. (1987).

S2. Experimental

Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb. Lanthanum (III) nitrate hexahydrate (216.4 mg, 0.5 mmol), 1-hydroxy-2-acetylamidopyridine (151.2 mg, 1 mmol) and distilled water (3 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 443 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colorless solution was decanted from small colorless crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.

S3. Refinement

H3A, H3B (for OH₂) and H2A, H2B (for NH₂) were located in difference syntheses and refined isotropically [O—H = 0.86 (2) and 0.86 (4) Å, U_iso(H) = 0.099 (14) and 0.121 (17) Ų; N—H = 0.883 (18) and 0.887 (17) Å, U_iso(H) = 0.088 (11) and 0.086 (11) Ų]. The remaining H atoms were positioned geometrically, with O—H = 0.82 Å (for OH) and C—H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms, with U_iso(H) = xU_eq(C,O), where x = 1.2 for aromatic H and x = 1.5 for OH H atoms.

Computing details

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

Figures

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

2-(1-Hydroxy-2-pyridyl)acetamide monohydrate

Crystal data

C7H7N2O2·H2O	F(000) = 356
Mr = 169.16	Dx = 1.483 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1902 reflections
a = 12.998 (3) Å	θ = 2.7–28.0°
b = 4.0992 (11) Å	µ = 0.12 mm^−1
c = 15.581 (4) Å	T = 273 K
β = 114.159 (5)°	Prism, colourless
V = 757.5 (3) Å^3	0.64 × 0.13 × 0.09 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	1611 independent reflections
Radiation source: fine-focus sealed tube	896 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
φ and ω scans	θmax = 27.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→15
Tmin = 0.929, Tmax = 0.990	k = −5→4
4820 measured reflections	l = −19→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.187	w = 1/[σ^2(Fo^2) + (0.1181P)^2 + 0.01P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
1611 reflections	Δρmax = 0.56 e Å^−3
127 parameters	Δρmin = −0.21 e Å^−3
7 restraints	Extinction correction: SHELXTL (Siemens, 1996), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.050 (19)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.63246 (18)	0.9693 (6)	0.06578 (17)	0.0777 (8)
H1A	0.6007	0.8559	0.0909	0.117*
O2	0.82022 (17)	1.1177 (6)	−0.13760 (13)	0.0687 (7)
O3	0.5047 (2)	0.5292 (7)	0.10867 (16)	0.0724 (7)
H3A	0.507 (3)	0.354 (5)	0.079 (2)	0.099 (14)*
H3B	0.551 (3)	0.631 (7)	0.092 (3)	0.121 (17)*
N1	0.73275 (19)	0.8485 (6)	0.08390 (17)	0.0551 (7)
N2	0.6565 (2)	1.3944 (7)	−0.19117 (18)	0.0645 (8)
H2A	0.660 (3)	1.481 (8)	−0.2419 (18)	0.088 (11)*
H2B	0.597 (2)	1.479 (8)	−0.185 (2)	0.086 (11)*
C1	0.7882 (3)	0.6667 (8)	0.1618 (2)	0.0651 (9)
H1	0.7541	0.6275	0.2028	0.078*
C2	0.8904 (3)	0.5416 (8)	0.1817 (2)	0.0643 (9)
H2	0.9268	0.4154	0.2353	0.077*
C3	0.9408 (3)	0.6049 (8)	0.1203 (2)	0.0651 (9)
H3	1.0123	0.5230	0.1330	0.078*
C4	0.8851 (2)	0.7890 (8)	0.0404 (2)	0.0567 (8)
H4	0.9188	0.8263	−0.0011	0.068*
C5	0.7793 (2)	0.9193 (7)	0.02133 (19)	0.0507 (7)
C6	0.71272 (18)	1.1137 (6)	−0.05215 (15)	0.0363 (6)
C7	0.7356 (2)	1.2057 (7)	−0.12975 (19)	0.0523 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0782 (15)	0.0862 (17)	0.0987 (17)	0.0263 (12)	0.0668 (14)	0.0342 (13)
O2	0.0629 (13)	0.0955 (18)	0.0645 (14)	−0.0075 (11)	0.0432 (11)	−0.0086 (11)
O3	0.0850 (16)	0.0765 (17)	0.0741 (15)	0.0080 (13)	0.0512 (13)	0.0056 (13)
N1	0.0585 (14)	0.0589 (15)	0.0633 (15)	0.0061 (11)	0.0406 (12)	0.0056 (12)
N2	0.0637 (17)	0.083 (2)	0.0563 (16)	−0.0042 (14)	0.0336 (14)	0.0096 (14)
C1	0.082 (2)	0.065 (2)	0.0635 (18)	0.0092 (16)	0.0453 (17)	0.0103 (16)
C2	0.0676 (19)	0.066 (2)	0.0581 (18)	0.0012 (15)	0.0241 (15)	0.0017 (15)
C3	0.0515 (16)	0.065 (2)	0.078 (2)	−0.0033 (14)	0.0250 (16)	−0.0090 (17)
C4	0.0501 (15)	0.068 (2)	0.0609 (17)	−0.0097 (13)	0.0311 (14)	−0.0064 (15)
C5	0.0550 (15)	0.0537 (17)	0.0552 (16)	−0.0160 (13)	0.0346 (13)	−0.0148 (13)
C6	0.0392 (12)	0.0416 (14)	0.0351 (12)	−0.0058 (10)	0.0223 (10)	0.0023 (10)
C7	0.0545 (16)	0.0630 (18)	0.0484 (15)	−0.0183 (14)	0.0302 (13)	−0.0124 (14)

Geometric parameters (Å, º)

O1—N1	1.313 (3)	C1—C2	1.337 (4)
O1—H1A	0.8200	C1—H1	0.9300
O2—C7	1.210 (3)	C2—C3	1.386 (4)
O3—H3A	0.86 (2)	C2—H2	0.9300
O3—H3B	0.86 (4)	C3—C4	1.381 (4)
N1—C1	1.353 (4)	C3—H3	0.9300
N1—C5	1.373 (3)	C4—C5	1.388 (4)
N2—C7	1.329 (4)	C4—H4	0.9300
N2—H2A	0.883 (18)	C5—C6	1.373 (4)
N2—H2B	0.887 (17)	C6—C7	1.410 (3)
N1—O1—H1A	109.5	C4—C3—C2	120.2 (3)
H3A—O3—H3B	94 (3)	C4—C3—H3	119.9
O1—N1—C1	121.2 (2)	C2—C3—H3	119.9
O1—N1—C5	117.1 (2)	C3—C4—C5	120.7 (3)
C1—N1—C5	121.7 (2)	C3—C4—H4	119.6
C7—N2—H2B	127 (2)	C5—C4—H4	119.6
C7—N2—H2A	125 (2)	C6—C5—N1	113.8 (2)
H2B—N2—H2A	108 (2)	C6—C5—C4	129.3 (2)
C2—C1—N1	122.3 (3)	N1—C5—C4	116.9 (3)
C2—C1—H1	118.9	C5—C6—C7	126.0 (2)
N1—C1—H1	118.9	O2—C7—N2	124.6 (3)
C1—C2—C3	118.2 (3)	O2—C7—C6	121.8 (3)
C1—C2—H2	120.9	N2—C7—C6	113.6 (2)
C3—C2—H2	120.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···N1	0.86 (4)	2.58 (4)	3.404 (3)	163 (4)
O3—H3B···O1	0.86 (4)	1.89 (4)	2.715 (3)	162 (4)
O1—H1A···O3	0.82	1.93	2.715 (3)	161
N2—H2A···O2^i	0.88 (2)	2.08 (2)	2.951 (3)	171 (3)
N2—H2B···O3^ii	0.89 (2)	2.11 (2)	2.888 (4)	146 (3)
O3—H3A···O1^iii	0.86 (2)	2.61 (3)	3.282 (4)	137 (3)
O3—H3A···O1^iv	0.86 (2)	2.34 (2)	3.063 (3)	142 (3)

Symmetry codes: (i) −x+3/2, y+1/2, −z−1/2; (ii) −x+1, −y+2, −z; (iii) −x+1, −y+1, −z; (iv) x, y−1, z.