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The molecule of the title compound, C4H5NO3, is planar (mean deviation of non-H atoms 0.03 Å). The N-C bond lengths are significantly different [1.365 (2) and 1.392 (2) Å]. The C=O group associated with the shorter N-C bond accepts a classical intermolecular hydrogen bond from the hydroxy H atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025704/bt6380sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025704/bt6380Isup2.hkl
Contains datablock I

CCDC reference: 227892

Key indicators

  • Single-crystal X-ray study
  • T = 133 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.108
  • Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.36 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 30.01 From the CIF: _reflns_number_total 860 Count of symmetry unique reflns 861 Completeness (_total/calc) 99.88% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C4H5NO3Dx = 1.563 Mg m3
Mr = 115.09Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 3627 reflections
a = 5.4266 (8) Åθ = 2.8–30.5°
b = 7.2419 (12) ŵ = 0.14 mm1
c = 12.445 (2) ÅT = 133 K
V = 489.09 (13) Å3Irregular tablet, colourless
Z = 40.30 × 0.25 × 0.10 mm
F(000) = 240
Data collection top
Bruker SMART 1000 CCD
diffractometer
803 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.071
Graphite monochromatorθmax = 30.0°, θmin = 3.3°
Detector resolution: 8.192 pixels mm-1h = 77
ω scansk = 1010
5566 measured reflectionsl = 1717
860 independent reflections
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0857P)2 + 0.0226P]
where P = (Fo2 + 2Fc2)/3
860 reflections(Δ/σ)max < 0.001
77 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.20 e Å3
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.

The anomalous dispersion effects were not significant and Friedel opposite reflections were therefore merged. The Flack parameter is meaningless in such cases.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3418 (3)0.45792 (19)0.36706 (11)0.0183 (3)
C20.4766 (3)0.5929 (2)0.29615 (11)0.0210 (3)
H2A0.36750.69660.27550.025*
H2B0.53670.53140.23010.025*
C30.6938 (3)0.6623 (2)0.36469 (12)0.0222 (3)
H3A0.85270.62130.33370.027*
H3B0.69340.79880.36890.027*
C40.6549 (3)0.5788 (2)0.47386 (13)0.0210 (3)
N0.4578 (2)0.45687 (16)0.46436 (10)0.0189 (3)
O10.1590 (2)0.36643 (15)0.34513 (9)0.0232 (3)
O20.7672 (3)0.60296 (19)0.55634 (10)0.0321 (3)
O30.3621 (2)0.36006 (16)0.54995 (9)0.0237 (3)
H00.494 (7)0.282 (4)0.575 (2)0.063 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0211 (6)0.0130 (6)0.0208 (6)0.0023 (5)0.0012 (5)0.0006 (5)
C20.0271 (7)0.0155 (6)0.0203 (6)0.0023 (6)0.0009 (6)0.0007 (5)
C30.0209 (6)0.0181 (6)0.0277 (7)0.0007 (6)0.0006 (6)0.0036 (5)
C40.0208 (6)0.0147 (6)0.0274 (7)0.0000 (6)0.0018 (6)0.0018 (5)
N0.0209 (6)0.0149 (5)0.0208 (6)0.0008 (5)0.0006 (5)0.0037 (4)
O10.0240 (5)0.0220 (5)0.0236 (5)0.0038 (5)0.0010 (5)0.0013 (4)
O20.0356 (7)0.0299 (7)0.0307 (6)0.0073 (5)0.0109 (6)0.0037 (5)
O30.0254 (6)0.0231 (6)0.0227 (5)0.0005 (5)0.0017 (5)0.0081 (4)
Geometric parameters (Å, º) top
C1—O11.224 (2)N—O31.3769 (16)
C1—N1.365 (2)C2—H2A0.9900
C1—C21.507 (2)C2—H2B0.9900
C2—C31.539 (2)C3—H3A0.9900
C3—C41.502 (2)C3—H3B0.9900
C4—O21.207 (2)O3—H00.97 (3)
C4—N1.392 (2)
O1—C1—N124.65 (13)C1—C2—H2A110.7
O1—C1—C2127.90 (13)C3—C2—H2A110.7
N—C1—C2107.44 (12)C1—C2—H2B110.7
C1—C2—C3105.01 (13)C3—C2—H2B110.7
C4—C3—C2105.20 (12)H2A—C2—H2B108.8
O2—C4—N123.54 (14)C4—C3—H3A110.7
O2—C4—C3129.80 (14)C2—C3—H3A110.7
N—C4—C3106.65 (13)C4—C3—H3B110.7
C1—N—O3121.03 (12)C2—C3—H3B110.7
C1—N—C4115.22 (12)H3A—C3—H3B108.8
O3—N—C4123.17 (12)N—O3—H0105.7 (18)
O1—C1—C2—C3178.69 (15)O1—C1—N—C4176.73 (14)
N—C1—C2—C32.65 (16)C2—C1—N—C41.98 (17)
C1—C2—C3—C45.83 (16)O2—C4—N—C1175.34 (16)
C2—C3—C4—O2174.31 (18)C3—C4—N—C15.86 (17)
C2—C3—C4—N6.99 (16)O2—C4—N—O34.0 (2)
O1—C1—N—O35.2 (2)C3—C4—N—O3177.16 (12)
C2—C1—N—O3173.48 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H0···O1i0.97 (3)1.71 (3)2.6442 (16)161 (3)
C3—H3A···O1ii0.992.493.320 (2)142
C2—H2B···O2iii0.992.603.585 (2)174
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x+1, y, z; (iii) x+3/2, y+1, z1/2.
 

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