organic compounds
The redetermined structure of the title compound, C4H9NO2, comprises a simple amino acid derivative arranged in an extensive hydrogen-bonded network, with the three hydrogen-bond donor elements (N—H) associating with the two hydrogen-bond acceptor elements (carboxylate O atoms). The addition of one C—HO close contact results in both carboxylate O atoms being involved in three-centre hydrogen-bonding associations.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802009662/cv6117sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802009662/cv6117Isup2.hkl |
CCDC reference: 189881
Computing details top
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.
Crystal data top
NH4+·C4H5O2− | F(000) = 448 |
Mr = 103.12 | Dx = 1.265 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.6273 (8) Å | Cell parameters from 2205 reflections |
b = 9.0102 (8) Å | θ = 2.9–27.5° |
c = 11.3370 (7) Å | µ = 0.10 mm−1 |
β = 93.749 (6)° | T = 150 K |
V = 1083.2 (1) Å3 | Block, colourless |
Z = 8 | 0.30 × 0.10 × 0.08 mm |
Data collection top
Bruker-Nonius KappaCCD area-detector diffractometer | 1208 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 755 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.4°, θmin = 3.0° |
φ and ω scans | h = −13→11 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −10→11 |
Tmin = 0.970, Tmax = 0.992 | l = −14→13 |
3853 measured reflections |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.0628P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
1208 reflections | Δρmax = 0.17 e Å−3 |
79 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.013 (3) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.6110 (1) | 0.0816 (1) | 0.16015 (9) | 0.0349 (4) | |
O2 | 0.7255 (1) | −0.1208 (2) | 0.13672 (9) | 0.0450 (5) | |
N1 | 0.6528 (1) | 0.1015 (2) | 0.3894 (1) | 0.0295 (4) | |
H1 | 0.674 (2) | 0.092 (2) | 0.480 (2) | 0.059 (6)* | |
H2 | 0.564 (2) | 0.103 (2) | 0.366 (2) | 0.046 (6)* | |
H3 | 0.691 (2) | 0.193 (3) | 0.364 (2) | 0.059 (7)* | |
C1 | 0.6794 (2) | −0.0217 (2) | 0.1983 (1) | 0.0283 (5) | |
C2 | 0.7096 (2) | −0.0321 (2) | 0.3335 (1) | 0.0281 (5) | |
C3 | 0.6450 (2) | −0.1696 (2) | 0.3791 (1) | 0.0350 (5) | |
H31 | 0.6549 | −0.1716 | 0.4657 | 0.044* | |
H32 | 0.6834 | −0.2587 | 0.3473 | 0.044* | |
H33 | 0.5551 | −0.1670 | 0.3538 | 0.044* | |
C4 | 0.8514 (2) | −0.0314 (2) | 0.3654 (2) | 0.0418 (6) | |
H41 | 0.8887 | 0.0585 | 0.3338 | 0.052* | |
H42 | 0.8898 | −0.1191 | 0.3313 | 0.052* | |
H43 | 0.8668 | −0.0332 | 0.4516 | 0.052* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0400 (8) | 0.0380 (8) | 0.0264 (7) | 0.0044 (6) | −0.0004 (5) | 0.0065 (5) |
O2 | 0.0717 (11) | 0.0413 (9) | 0.0219 (7) | 0.0169 (7) | 0.0017 (6) | −0.0034 (6) |
N1 | 0.0389 (11) | 0.0276 (10) | 0.0216 (8) | −0.0011 (7) | −0.0007 (6) | −0.0021 (6) |
C1 | 0.0357 (10) | 0.0298 (11) | 0.0194 (9) | −0.0041 (8) | 0.0009 (7) | 0.0005 (7) |
C2 | 0.0367 (11) | 0.0271 (10) | 0.0200 (8) | 0.0029 (8) | −0.0009 (7) | −0.0025 (7) |
C3 | 0.0506 (13) | 0.0290 (11) | 0.0252 (9) | 0.0047 (9) | 0.0015 (8) | 0.0035 (7) |
C4 | 0.0395 (12) | 0.0497 (14) | 0.0351 (10) | 0.0040 (10) | −0.0041 (8) | −0.0003 (9) |
Geometric parameters (Å, º) top
O1—C1 | 1.241 (2) | C2—C4 | 1.527 (2) |
O2—C1 | 1.252 (2) | C3—H31 | 0.98 |
N1—C2 | 1.505 (2) | C3—H32 | 0.98 |
N1—H1 | 1.04 (2) | C3—H33 | 0.98 |
N1—H2 | 0.96 (2) | C4—H41 | 0.98 |
N1—H3 | 0.97 (3) | C4—H42 | 0.98 |
C1—C2 | 1.549 (2) | C4—H43 | 0.98 |
C2—C3 | 1.523 (3) | ||
C2—N1—H1 | 106 (1) | C4—C2—C1 | 111.8 (1) |
C2—N1—H2 | 108 (1) | C2—C3—H31 | 109.5 |
H1—N1—H2 | 115 (2) | C2—C3—H32 | 109.5 |
C2—N1—H3 | 111 (1) | H31—C3—H32 | 109.5 |
H1—N1—H3 | 107 (2) | C2—C3—H33 | 109.5 |
H2—N1—H3 | 109 (2) | H31—C3—H33 | 109.5 |
O1—C1—O2 | 125.6 (1) | H32—C3—H33 | 109.5 |
O1—C1—C2 | 117.9 (1) | C2—C4—H41 | 109.5 |
O2—C1—C2 | 116.5 (2) | C2—C4—H42 | 109.5 |
N1—C2—C3 | 107.8 (1) | H41—C4—H42 | 109.5 |
N1—C2—C4 | 108.3 (1) | C2—C4—H43 | 109.5 |
C3—C2—C4 | 112.5 (2) | H41—C4—H43 | 109.5 |
N1—C2—C1 | 107.8 (1) | H42—C4—H43 | 109.5 |
C3—C2—C1 | 108.5 (1) | ||
O1—C1—C2—N1 | −4.5 (2) | O2—C1—C2—C3 | −67.1 (2) |
O2—C1—C2—N1 | 176.4 (2) | O1—C1—C2—C4 | −123.5 (2) |
O1—C1—C2—C3 | 111.9 (2) | O2—C1—C2—C4 | 57.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 1.04 (2) | 1.84 (2) | 2.8645 (18) | 167 (2) |
N1—H2···O1ii | 0.96 (2) | 1.88 (2) | 2.828 (2) | 170 (2) |
N1—H3···O2iii | 0.97 (3) | 1.90 (3) | 2.841 (2) | 163 (2) |
C3—H31···O1i | 0.98 | 2.42 | 3.326 (2) | 153 |
Symmetry codes: (i) x, −y, z+1/2; (ii) −x+1, y, −z+1/2; (iii) −x+3/2, y+1/2, −z+1/2. |