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The asymmetric unit of the title compound, C4H10N2O3·H2O, contains one zwitterionic organic molecule and two half-molecules of water, the O atoms of which lie on a twofold axis. Intermolecular hydrogen bonds involving the water molecules, the ammonium cationic group and the carboxylate group link the molecules into an extended three-dimensional network.
Supporting information
CCDC reference: 628075
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.051
- wR factor = 0.149
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
1 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
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000) and DIAMOND (Brandenburg, 2004); software used to prepare material for publication: SHELXTL.
(3-Ammonio-2-hydroxypropyl)carbamate monohydrate
top
Crystal data top
C4H10N2O3·H2O | F(000) = 328 |
Mr = 152.16 | Dx = 1.422 Mg m−3 |
Monoclinic, P2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yc | Cell parameters from 2364 reflections |
a = 8.500 (3) Å | θ = 2.6–26.4° |
b = 5.950 (2) Å | µ = 0.13 mm−1 |
c = 15.665 (4) Å | T = 298 K |
β = 116.204 (15)° | Block, pale yellow |
V = 710.8 (4) Å3 | 0.36 × 0.16 × 0.11 mm |
Z = 4 | |
Data collection top
Bruck SMART CCD area-detector diffractometer | 1253 independent reflections |
Radiation source: fine-focus sealed tube | 768 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
φ and ω scans | θmax = 25.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→9 |
Tmin = 0.966, Tmax = 0.986 | k = −7→6 |
3521 measured reflections | l = −18→18 |
Refinement top
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0638P)2 + 0.5606P] where P = (Fo2 + 2Fc2)/3 |
1253 reflections | (Δ/σ)max < 0.001 |
92 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Special details top
Experimental. Spectroscopic analysis: 1H NMR (D2O, δ, p.p.m.): 3.23 (m, 2H), 3.61 (m,
2H), 4.47 (m, 2H). Elemental analysis, calculated for C4H10N2O3: C
35.82, H 7.51, N 20.88%; found: C 35.96, H 7.62, N 20.48%. ESI-MS (–P)
m/z = 133.1. |
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 (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.7394 (3) | 0.4616 (4) | 0.91221 (16) | 0.0581 (8) | |
H1A | 0.7134 | 0.3948 | 0.8620 | 0.070* | |
O2 | 0.6935 (3) | 0.6946 (4) | 0.60410 (14) | 0.0425 (6) | |
O3 | 0.6954 (3) | 0.9983 (3) | 0.68671 (14) | 0.0393 (6) | |
N1 | 0.8149 (4) | 0.6769 (4) | 0.76347 (17) | 0.0391 (7) | |
H1 | 0.8420 | 0.5395 | 0.7593 | 0.047* | |
N2 | 0.6578 (3) | 0.7408 (4) | 1.03015 (17) | 0.0371 (7) | |
H2A | 0.6864 | 0.8120 | 1.0850 | 0.056* | |
H2B | 0.6669 | 0.5931 | 1.0402 | 0.056* | |
H2C | 0.5480 | 0.7750 | 0.9896 | 0.056* | |
C1 | 0.8632 (4) | 0.7653 (6) | 0.8579 (2) | 0.0377 (8) | |
H1B | 0.8673 | 0.9281 | 0.8560 | 0.045* | |
H1C | 0.9795 | 0.7121 | 0.9006 | 0.045* | |
C2 | 0.7345 (4) | 0.6949 (5) | 0.8963 (2) | 0.0360 (8) | |
H2 | 0.6157 | 0.7375 | 0.8503 | 0.043* | |
C3 | 0.7777 (4) | 0.8112 (6) | 0.9896 (2) | 0.0402 (8) | |
H3A | 0.8974 | 0.7762 | 1.0344 | 0.048* | |
H3B | 0.7691 | 0.9725 | 0.9798 | 0.048* | |
C4 | 0.7313 (4) | 0.7922 (5) | 0.6819 (2) | 0.0309 (7) | |
O4 | 0.5000 | 0.2400 (5) | 0.7500 | 0.0494 (9) | |
H5 | 0.5445 | 0.1692 | 0.7188 | 0.059* | |
O5 | 1.0000 | 0.2510 (5) | 0.7500 | 0.0601 (10) | |
H6 | 0.9100 | 0.1685 | 0.7348 | 0.072* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.095 (2) | 0.0408 (16) | 0.0434 (14) | −0.0045 (14) | 0.0346 (14) | −0.0010 (11) |
O2 | 0.0516 (14) | 0.0441 (15) | 0.0315 (12) | 0.0022 (11) | 0.0180 (11) | −0.0060 (10) |
O3 | 0.0527 (14) | 0.0294 (13) | 0.0389 (13) | 0.0069 (10) | 0.0231 (11) | 0.0026 (10) |
N1 | 0.0542 (17) | 0.0315 (15) | 0.0332 (15) | 0.0093 (13) | 0.0209 (13) | 0.0036 (12) |
N2 | 0.0516 (17) | 0.0304 (15) | 0.0296 (13) | −0.0011 (13) | 0.0182 (12) | −0.0022 (11) |
C1 | 0.0396 (18) | 0.043 (2) | 0.0294 (16) | −0.0002 (15) | 0.0143 (14) | 0.0010 (14) |
C2 | 0.0450 (19) | 0.0300 (19) | 0.0316 (17) | −0.0027 (14) | 0.0156 (15) | −0.0010 (13) |
C3 | 0.046 (2) | 0.040 (2) | 0.0323 (18) | −0.0090 (15) | 0.0154 (16) | −0.0055 (14) |
C4 | 0.0288 (16) | 0.0347 (19) | 0.0327 (17) | −0.0008 (14) | 0.0168 (14) | 0.0008 (14) |
O4 | 0.066 (2) | 0.0372 (19) | 0.062 (2) | 0.000 | 0.0441 (19) | 0.000 |
O5 | 0.052 (2) | 0.0325 (19) | 0.089 (3) | 0.000 | 0.025 (2) | 0.000 |
Geometric parameters (Å, º) top
O1—C2 | 1.408 (4) | N2—H2C | 0.8900 |
O1—H1A | 0.8204 | C1—C2 | 1.522 (4) |
O2—C4 | 1.257 (3) | C1—H1B | 0.9700 |
O3—C4 | 1.274 (3) | C1—H1C | 0.9700 |
N1—C4 | 1.344 (4) | C2—C3 | 1.508 (4) |
N1—C1 | 1.448 (4) | C2—H2 | 0.9800 |
N1—H1 | 0.8597 | C3—H3A | 0.9700 |
N2—C3 | 1.479 (4) | C3—H3B | 0.9700 |
N2—H2A | 0.8900 | O4—H5 | 0.8501 |
N2—H2B | 0.8900 | O5—H6 | 0.8497 |
| | | |
C2—O1—H1A | 109.5 | O1—C2—C3 | 107.8 (3) |
C4—N1—C1 | 125.3 (3) | O1—C2—C1 | 111.8 (3) |
C4—N1—H1 | 117.4 | C3—C2—C1 | 110.3 (3) |
C1—N1—H1 | 117.3 | O1—C2—H2 | 109.0 |
C3—N2—H2A | 109.5 | C3—C2—H2 | 109.0 |
C3—N2—H2B | 109.5 | C1—C2—H2 | 109.0 |
H2A—N2—H2B | 109.5 | N2—C3—C2 | 111.6 (3) |
C3—N2—H2C | 109.5 | N2—C3—H3A | 109.3 |
H2A—N2—H2C | 109.5 | C2—C3—H3A | 109.3 |
H2B—N2—H2C | 109.5 | N2—C3—H3B | 109.3 |
N1—C1—C2 | 112.0 (3) | C2—C3—H3B | 109.3 |
N1—C1—H1B | 109.2 | H3A—C3—H3B | 108.0 |
C2—C1—H1B | 109.2 | O2—C4—O3 | 122.5 (3) |
N1—C1—H1C | 109.2 | O2—C4—N1 | 119.2 (3) |
C2—C1—H1C | 109.2 | O3—C4—N1 | 118.3 (3) |
H1B—C1—H1C | 107.9 | | |
| | | |
C4—N1—C1—C2 | 99.8 (4) | C1—C2—C3—N2 | −178.3 (3) |
N1—C1—C2—O1 | 66.5 (3) | C1—N1—C4—O2 | −178.5 (3) |
N1—C1—C2—C3 | −173.6 (3) | C1—N1—C4—O3 | 2.4 (4) |
O1—C2—C3—N2 | −56.0 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2C···O2i | 0.89 | 1.98 | 2.805 (3) | 153 |
N2—H2B···O2ii | 0.89 | 1.95 | 2.799 (3) | 160 |
N2—H2A···O3iii | 0.89 | 1.93 | 2.799 (3) | 166 |
O4—H5···O3iv | 0.85 | 1.87 | 2.695 (3) | 163 |
O5—H6···O3iv | 0.85 | 1.93 | 2.772 (3) | 174 |
N1—H1···O5 | 0.86 | 2.22 | 3.039 (4) | 158 |
O1—H1A···O4 | 0.82 | 2.10 | 2.787 (3) | 141 |
N2—H2B···O1 | 0.89 | 2.47 | 2.790 (3) | 102 |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x, −y+1, z+1/2; (iii) x, −y+2, z+1/2; (iv) x, y−1, z. |
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