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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804015302/lh6219sup1.cif
Contains datablocks gloabl, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804015302/lh6219Isup2.hkl
Contains datablock I

CCDC reference: 248770

Key indicators

  • Single-crystal X-ray study
  • T = 126 K
  • Mean [sigma](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

Computing details top

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.

(I) top
Crystal data top
C8H9NO3·H2OF(000) = 392.00
Mr = 185.18Dx = 1.499 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ynCell parameters from 1569 reflections
a = 7.2905 (8) Åθ = 2.8–24.5°
b = 9.481 (1) ŵ = 0.12 mm1
c = 11.886 (1) ÅT = 126 K
β = 93.280 (2)°Block, colorless
V = 820.3 (2) Å30.40 × 0.30 × 0.15 mm
Z = 4
Data collection top
Bruker SMART 1000
diffractometer
1016 reflections with F2 > 3σ(F2)
ω scansRint = 0.031
Absorption correction: empirical (using intensity measurements)
(Blessing, 1995)
θmax = 24.7°
Tmin = 0.572, Tmax = 0.982h = 84
3625 measured reflectionsk = 1010
1335 independent reflectionsl = 1313
Refinement top
Refinement on FH 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 = 2.02Δρmax = 0.21 e Å3
1016 reflectionsΔρmin = 0.34 e Å3
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
xyzUiso*/Ueq
O10.2409 (2)0.1992 (2)0.0660 (1)0.0230 (5)
O20.3749 (2)0.3971 (2)0.0656 (1)0.0258 (5)
O30.1469 (2)0.0526 (2)0.0972 (1)0.0215 (5)
O40.5149 (3)0.6187 (2)0.1840 (1)0.0243 (5)
N10.2362 (3)0.2262 (2)0.0225 (2)0.0192 (6)
C10.3072 (3)0.0176 (2)0.0742 (2)0.0157 (6)
C20.3082 (3)0.1585 (2)0.0382 (2)0.0170 (7)
C30.3796 (3)0.2645 (2)0.1099 (2)0.0177 (6)
C40.4498 (3)0.2303 (2)0.2164 (2)0.0198 (7)
C50.4511 (3)0.0908 (2)0.2527 (2)0.0196 (7)
C60.3805 (3)0.0142 (2)0.1825 (2)0.0189 (6)
C70.2268 (3)0.0896 (2)0.0050 (2)0.0172 (7)
C80.1560 (3)0.3333 (2)0.0533 (2)0.0228 (7)
H10.195 (3)0.116 (3)0.100 (2)0.0240*
H20.423 (3)0.452 (2)0.114 (2)0.0240*
H30.304 (3)0.251 (2)0.088 (2)0.0230*
H40.49760.30230.26530.0237*
H50.50060.06780.32610.0235*
H60.38180.10920.20800.0227*
H70.20790.32580.12460.0273*
H80.02690.31970.06210.0273*
H90.18110.42420.02250.0273*
H100.561 (3)0.611 (2)0.260 (2)0.0240*
H110.599 (3)0.654 (3)0.150 (2)0.0240*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.035 (1)0.0185 (9)0.0149 (9)0.0021 (7)0.0076 (8)0.0014 (7)
O20.041 (1)0.0139 (9)0.0214 (9)0.0034 (7)0.0071 (8)0.0002 (7)
O30.028 (1)0.0187 (9)0.0164 (9)0.0004 (7)0.0051 (7)0.0006 (7)
O40.034 (1)0.0213 (9)0.0178 (9)0.0050 (8)0.0012 (8)0.0023 (8)
N10.026 (1)0.015 (1)0.016 (1)0.0008 (8)0.0025 (9)0.0001 (9)
C10.015 (1)0.018 (1)0.014 (1)0.0007 (10)0.0019 (10)0.0012 (10)
C20.018 (1)0.020 (1)0.013 (1)0.002 (1)0.000 (1)0.0018 (10)
C30.020 (1)0.014 (1)0.019 (1)0.0008 (10)0.002 (1)0.001 (1)
C40.021 (1)0.021 (1)0.018 (1)0.001 (1)0.000 (1)0.005 (1)
C50.024 (1)0.022 (1)0.013 (1)0.002 (1)0.002 (1)0.0021 (10)
C60.022 (1)0.018 (1)0.017 (1)0.002 (1)0.003 (1)0.0020 (10)
C70.015 (1)0.020 (1)0.017 (1)0.0000 (10)0.005 (1)0.0008 (10)
C80.029 (2)0.016 (1)0.023 (1)0.002 (1)0.002 (1)0.0027 (10)
Geometric parameters (Å, º) top
O1—C21.362 (3)O1—H10.94 (2)
O2—C31.363 (3)O2—H20.84 (2)
O3—C71.262 (3)O4—H100.95 (2)
N1—C71.336 (3)O4—H110.82 (2)
N1—C81.457 (3)N1—H30.93 (2)
C1—C21.403 (3)C4—H40.950
C1—C61.397 (3)C5—H50.950
C1—C71.483 (3)C6—H60.950
C2—C31.399 (3)C8—H70.950
C3—C41.376 (3)C8—H80.950
C4—C51.391 (3)C8—H90.950
C5—C61.380 (3)
O1···O32.506 (2)O3···O12.506 (2)
O1···O22.598 (2)O3···O4iv2.792 (2)
O1···O4i2.899 (2)O3···O3ii3.391 (3)
O1···N1ii3.555 (3)O4···O22.697 (2)
O2···O12.598 (2)O4···O3v2.792 (2)
O2···O42.697 (2)O4···O1i2.899 (2)
O2···O4i3.121 (2)O4···N1vi3.087 (3)
O2···O2i3.145 (3)O4···O2i3.121 (2)
O2···N1iii3.479 (3)
C7—N1—C8120.7 (2)C3—O2—H2107 (1)
C2—C1—C6118.6 (2)H10—O4—H11105 (2)
C2—C1—C7117.9 (2)C7—N1—H3118 (1)
C6—C1—C7123.6 (2)C8—N1—H3120 (1)
O1—C2—C1122.7 (2)C3—C4—H4119.821
O1—C2—C3116.9 (2)C5—C4—H4119.822
C1—C2—C3120.4 (2)C4—C5—H5119.915
O2—C3—C2115.3 (2)C6—C5—H5119.914
O2—C3—C4125.0 (2)C1—C6—H6119.632
C2—C3—C4119.8 (2)C5—C6—H6119.632
C3—C4—C5120.4 (2)N1—C8—H7109.471
C4—C5—C6120.2 (2)N1—C8—H8109.470
C1—C6—C5120.7 (2)N1—C8—H9109.469
O3—C7—N1119.8 (2)H7—C8—H8109.473
O3—C7—C1120.5 (2)H7—C8—H9109.472
N1—C7—C1119.7 (2)H8—C8—H9109.472
C2—O1—H1104 (1)
O1—C2—C1—C6179.6 (2)N1—C7—C1—C65.7 (3)
O1—C2—C1—C70.8 (3)C1—C2—C3—C40.2 (3)
O1—C2—C3—O20.8 (3)C1—C6—C5—C40.1 (3)
O1—C2—C3—C4180.0 (2)C1—C7—N1—C8179.2 (2)
O2—C3—C2—C1179.4 (2)C2—C1—C6—C50.5 (3)
O2—C3—C4—C5178.8 (2)C2—C3—C4—C50.4 (4)
O3—C7—N1—C80.4 (3)C3—C2—C1—C60.6 (3)
O3—C7—C1—C26.5 (3)C3—C2—C1—C7179.0 (2)
O3—C7—C1—C6173.1 (2)C3—C4—C5—C60.5 (3)
N1—C7—C1—C2174.7 (2)C5—C6—C1—C7179.1 (2)
Symmetry codes: (i) x+1, y1, z; (ii) x, y, z; (iii) x+1, y, z; (iv) x1/2, y1/2, z1/2; (v) x+1/2, y1/2, z+1/2; (vi) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H11···O1i0.82 (2)2.10 (3)2.899 (2)162 (2)
O4—H10···O3v0.95 (2)1.86 (2)2.792 (2)167 (2)
O2—H2···O40.84 (2)1.89 (2)2.697 (2)160 (2)
O1—H1···O30.94 (2)1.64 (3)2.506 (2)151 (2)
N1—H3···O4vii0.93 (2)2.23 (2)3.087 (3)152 (2)
Symmetry codes: (i) x+1, y1, z; (v) x+1/2, y1/2, z+1/2; (vii) x, y+1, z.
 

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