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The title compound, C8H9NO3·H2O, is a monohydrate. The molecules pack in pairs of planes, each pair of planes held together by a two-dimensional hydrogen-bonding network.
Supporting information
CCDC reference: 248770
Key indicators
- Single-crystal X-ray study
- T = 126 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.052
- Data-to-parameter ratio = 7.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.66 Deg.
| Author Response: Due to a rapid drop-off in intensity of the data at high angle,
we were unable to collect data to the limits recommended by checkCIF.
Presumbaly this was due to poor ordering of the molecules, possibly the
presence of the hydrogen-bonded water network caused this problem.
|
In addition, this resulted in a lower than normal number of data to refine
against leading to a relatively poor data to parameter ratio and several other
level C alerts (for example sin(theta/lambda)).
The slightly high Goodness-of-Fit value (2.024) results from refinement
against F, rather than F^2.
The T(min) and T(max) values reported were normalized, hence are a ratio.
If there are any questions regarding the dataset, please do not hesitate to
contact us.
Alert level B
ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
Tmin and Tmax reported: 0.572 0.982
Tmin' and Tmax expected: 0.952 0.982
RR' = 0.601
Please check that your absorption correction is appropriate.
REFNR01_ALERT_3_B Ratio of reflections to parameters is < 8 for a
centrosymmetric structure
sine(theta)/lambda 0.5871
Proportion of unique data used 0.7610
Ratio reflections to parameters 7.6391
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.60
PLAT088_ALERT_3_B Poor Data / Parameter Ratio .................... 7.64
Alert level C
GOODF01_ALERT_2_C The least squares goodness of fit parameter lies
outside the range 0.80 <> 2.00
Goodness of fit given = 2.024
THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590
Calculated sin(theta_max)/wavelength = 0.5871
PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 24.66 Deg.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT087_ALERT_2_C Unsatisfactory S value (Too High) .............. 2.02
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
H2 O
1 ALERT level A = In general: serious problem
4 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
8 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation and Rigaku, 1998); molecular graphics: TEXSAN and PLATON (Spek, 2004); software used to prepare material for publication: TEXSAN.
Crystal data top
C8H9NO3·H2O | F(000) = 392.00 |
Mr = 185.18 | Dx = 1.499 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2yn | Cell parameters from 1569 reflections |
a = 7.2905 (8) Å | θ = 2.8–24.5° |
b = 9.481 (1) Å | µ = 0.12 mm−1 |
c = 11.886 (1) Å | T = 126 K |
β = 93.280 (2)° | Block, colorless |
V = 820.3 (2) Å3 | 0.40 × 0.30 × 0.15 mm |
Z = 4 | |
Data collection top
Bruker SMART 1000 diffractometer | 1016 reflections with F2 > 3σ(F2) |
ω scans | Rint = 0.031 |
Absorption correction: empirical (using intensity measurements) (Blessing, 1995) | θmax = 24.7° |
Tmin = 0.572, Tmax = 0.982 | h = −8→4 |
3625 measured reflections | k = −10→10 |
1335 independent reflections | l = −13→13 |
Refinement top
Refinement on F | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo) + 0.00022|Fo|2] |
wR(F2) = 0.052 | (Δ/σ)max = 0.0003 |
S = 2.02 | Δρmax = 0.21 e Å−3 |
1016 reflections | Δρmin = −0.34 e Å−3 |
133 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > 3.0 σ(F2). The
weighted R-factor (wR), goodness of fit (S) and
R-factor (gt) are based on F, with F set to zero for
negative F. The threshold expression of F2 > 3.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.2409 (2) | −0.1992 (2) | −0.0660 (1) | 0.0230 (5) | |
O2 | 0.3749 (2) | −0.3971 (2) | 0.0656 (1) | 0.0258 (5) | |
O3 | 0.1469 (2) | 0.0526 (2) | −0.0972 (1) | 0.0215 (5) | |
O4 | 0.5149 (3) | −0.6187 (2) | 0.1840 (1) | 0.0243 (5) | |
N1 | 0.2362 (3) | 0.2262 (2) | 0.0225 (2) | 0.0192 (6) | |
C1 | 0.3072 (3) | −0.0176 (2) | 0.0742 (2) | 0.0157 (6) | |
C2 | 0.3082 (3) | −0.1585 (2) | 0.0382 (2) | 0.0170 (7) | |
C3 | 0.3796 (3) | −0.2645 (2) | 0.1099 (2) | 0.0177 (6) | |
C4 | 0.4498 (3) | −0.2303 (2) | 0.2164 (2) | 0.0198 (7) | |
C5 | 0.4511 (3) | −0.0908 (2) | 0.2527 (2) | 0.0196 (7) | |
C6 | 0.3805 (3) | 0.0142 (2) | 0.1825 (2) | 0.0189 (6) | |
C7 | 0.2268 (3) | 0.0896 (2) | −0.0050 (2) | 0.0172 (7) | |
C8 | 0.1560 (3) | 0.3333 (2) | −0.0533 (2) | 0.0228 (7) | |
H1 | 0.195 (3) | −0.116 (3) | −0.100 (2) | 0.0240* | |
H2 | 0.423 (3) | −0.452 (2) | 0.114 (2) | 0.0240* | |
H3 | 0.304 (3) | 0.251 (2) | 0.088 (2) | 0.0230* | |
H4 | 0.4976 | −0.3023 | 0.2653 | 0.0237* | |
H5 | 0.5006 | −0.0678 | 0.3261 | 0.0235* | |
H6 | 0.3818 | 0.1092 | 0.2080 | 0.0227* | |
H7 | 0.2079 | 0.3258 | −0.1246 | 0.0273* | |
H8 | 0.0269 | 0.3197 | −0.0621 | 0.0273* | |
H9 | 0.1811 | 0.4242 | −0.0225 | 0.0273* | |
H10 | 0.561 (3) | −0.611 (2) | 0.260 (2) | 0.0240* | |
H11 | 0.599 (3) | −0.654 (3) | 0.150 (2) | 0.0240* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.035 (1) | 0.0185 (9) | 0.0149 (9) | 0.0021 (7) | −0.0076 (8) | −0.0014 (7) |
O2 | 0.041 (1) | 0.0139 (9) | 0.0214 (9) | 0.0034 (7) | −0.0071 (8) | −0.0002 (7) |
O3 | 0.028 (1) | 0.0187 (9) | 0.0164 (9) | −0.0004 (7) | −0.0051 (7) | 0.0006 (7) |
O4 | 0.034 (1) | 0.0213 (9) | 0.0178 (9) | 0.0050 (8) | −0.0012 (8) | −0.0023 (8) |
N1 | 0.026 (1) | 0.015 (1) | 0.016 (1) | 0.0008 (8) | −0.0025 (9) | −0.0001 (9) |
C1 | 0.015 (1) | 0.018 (1) | 0.014 (1) | 0.0007 (10) | 0.0019 (10) | 0.0012 (10) |
C2 | 0.018 (1) | 0.020 (1) | 0.013 (1) | −0.002 (1) | 0.000 (1) | −0.0018 (10) |
C3 | 0.020 (1) | 0.014 (1) | 0.019 (1) | 0.0008 (10) | 0.002 (1) | −0.001 (1) |
C4 | 0.021 (1) | 0.021 (1) | 0.018 (1) | 0.001 (1) | −0.000 (1) | 0.005 (1) |
C5 | 0.024 (1) | 0.022 (1) | 0.013 (1) | −0.002 (1) | −0.002 (1) | −0.0021 (10) |
C6 | 0.022 (1) | 0.018 (1) | 0.017 (1) | −0.002 (1) | 0.003 (1) | −0.0020 (10) |
C7 | 0.015 (1) | 0.020 (1) | 0.017 (1) | −0.0000 (10) | 0.005 (1) | 0.0008 (10) |
C8 | 0.029 (2) | 0.016 (1) | 0.023 (1) | 0.002 (1) | −0.002 (1) | 0.0027 (10) |
Geometric parameters (Å, º) top
O1—C2 | 1.362 (3) | O1—H1 | 0.94 (2) |
O2—C3 | 1.363 (3) | O2—H2 | 0.84 (2) |
O3—C7 | 1.262 (3) | O4—H10 | 0.95 (2) |
N1—C7 | 1.336 (3) | O4—H11 | 0.82 (2) |
N1—C8 | 1.457 (3) | N1—H3 | 0.93 (2) |
C1—C2 | 1.403 (3) | C4—H4 | 0.950 |
C1—C6 | 1.397 (3) | C5—H5 | 0.950 |
C1—C7 | 1.483 (3) | C6—H6 | 0.950 |
C2—C3 | 1.399 (3) | C8—H7 | 0.950 |
C3—C4 | 1.376 (3) | C8—H8 | 0.950 |
C4—C5 | 1.391 (3) | C8—H9 | 0.950 |
C5—C6 | 1.380 (3) | | |
| | | |
O1···O3 | 2.506 (2) | O3···O1 | 2.506 (2) |
O1···O2 | 2.598 (2) | O3···O4iv | 2.792 (2) |
O1···O4i | 2.899 (2) | O3···O3ii | 3.391 (3) |
O1···N1ii | 3.555 (3) | O4···O2 | 2.697 (2) |
O2···O1 | 2.598 (2) | O4···O3v | 2.792 (2) |
O2···O4 | 2.697 (2) | O4···O1i | 2.899 (2) |
O2···O4i | 3.121 (2) | O4···N1vi | 3.087 (3) |
O2···O2i | 3.145 (3) | O4···O2i | 3.121 (2) |
O2···N1iii | 3.479 (3) | | |
| | | |
C7—N1—C8 | 120.7 (2) | C3—O2—H2 | 107 (1) |
C2—C1—C6 | 118.6 (2) | H10—O4—H11 | 105 (2) |
C2—C1—C7 | 117.9 (2) | C7—N1—H3 | 118 (1) |
C6—C1—C7 | 123.6 (2) | C8—N1—H3 | 120 (1) |
O1—C2—C1 | 122.7 (2) | C3—C4—H4 | 119.821 |
O1—C2—C3 | 116.9 (2) | C5—C4—H4 | 119.822 |
C1—C2—C3 | 120.4 (2) | C4—C5—H5 | 119.915 |
O2—C3—C2 | 115.3 (2) | C6—C5—H5 | 119.914 |
O2—C3—C4 | 125.0 (2) | C1—C6—H6 | 119.632 |
C2—C3—C4 | 119.8 (2) | C5—C6—H6 | 119.632 |
C3—C4—C5 | 120.4 (2) | N1—C8—H7 | 109.471 |
C4—C5—C6 | 120.2 (2) | N1—C8—H8 | 109.470 |
C1—C6—C5 | 120.7 (2) | N1—C8—H9 | 109.469 |
O3—C7—N1 | 119.8 (2) | H7—C8—H8 | 109.473 |
O3—C7—C1 | 120.5 (2) | H7—C8—H9 | 109.472 |
N1—C7—C1 | 119.7 (2) | H8—C8—H9 | 109.472 |
C2—O1—H1 | 104 (1) | | |
| | | |
O1—C2—C1—C6 | −179.6 (2) | N1—C7—C1—C6 | 5.7 (3) |
O1—C2—C1—C7 | 0.8 (3) | C1—C2—C3—C4 | −0.2 (3) |
O1—C2—C3—O2 | 0.8 (3) | C1—C6—C5—C4 | −0.1 (3) |
O1—C2—C3—C4 | 180.0 (2) | C1—C7—N1—C8 | −179.2 (2) |
O2—C3—C2—C1 | −179.4 (2) | C2—C1—C6—C5 | −0.5 (3) |
O2—C3—C4—C5 | 178.8 (2) | C2—C3—C4—C5 | −0.4 (4) |
O3—C7—N1—C8 | −0.4 (3) | C3—C2—C1—C6 | 0.6 (3) |
O3—C7—C1—C2 | 6.5 (3) | C3—C2—C1—C7 | −179.0 (2) |
O3—C7—C1—C6 | −173.1 (2) | C3—C4—C5—C6 | 0.5 (3) |
N1—C7—C1—C2 | −174.7 (2) | C5—C6—C1—C7 | 179.1 (2) |
Symmetry codes: (i) −x+1, −y−1, −z; (ii) −x, −y, −z; (iii) −x+1, −y, −z; (iv) x−1/2, −y−1/2, z−1/2; (v) x+1/2, −y−1/2, z+1/2; (vi) x, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H11···O1i | 0.82 (2) | 2.10 (3) | 2.899 (2) | 162 (2) |
O4—H10···O3v | 0.95 (2) | 1.86 (2) | 2.792 (2) | 167 (2) |
O2—H2···O4 | 0.84 (2) | 1.89 (2) | 2.697 (2) | 160 (2) |
O1—H1···O3 | 0.94 (2) | 1.64 (3) | 2.506 (2) | 151 (2) |
N1—H3···O4vii | 0.93 (2) | 2.23 (2) | 3.087 (3) | 152 (2) |
Symmetry codes: (i) −x+1, −y−1, −z; (v) x+1/2, −y−1/2, z+1/2; (vii) x, y+1, z. |
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