organic compounds
The title compound, C3H5NO3, is used as a model system for studies of radiation damage in more complex polypeptides. The crystal structure is only the third of an isolated N-formyl amino acid. Essentially planar molecules form hydrogen-bonded sheets with three types of intermolecular interactions, including a very rare >N—HO hydrogen bond with the OH group of the carboxylic acid function as the acceptor.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804009122/bt6447sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804009122/bt6447Isup2.hkl |
CCDC reference: 239274
Key indicators
- Single-crystal X-ray study
- T = 105 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.122
- Data-to-parameter ratio = 12.0
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT063_ALERT_3_A Crystal Probably too Large for Beam Size ....... 1.10 mm
Author Response: This is no problem for a light atom structure, see Gorbitz, Acta Cryst. B55 (1999) 1090-98. |
Alert level B CRYSS02_ALERT_3_B The value of _exptl_crystal_size_mid is > 0.8 Mid crystal size given = 0.850 CRYSS02_ALERT_3_B The value of _exptl_crystal_size_max is > 1.0 Maximum crystal size given = 1.100
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.14 PLAT355_ALERT_3_C Long O-H Bond (0.82A) O2 - H2 ... 1.06 Ang.
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 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, 1998); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
N-formylglycine top
Crystal data top
C3H5NO3 | F(000) = 216 |
Mr = 103.08 | Dx = 1.579 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4378 (15) Å | Cell parameters from 1914 reflections |
b = 9.1650 (19) Å | θ = 3.1–27.1° |
c = 7.1002 (14) Å | µ = 0.14 mm−1 |
β = 116.348 (3)° | T = 105 K |
V = 433.72 (15) Å3 | Block, colourless |
Z = 4 | 1.10 × 0.85 × 0.50 mm |
Data collection top
Siemens SMART CCD diffractometer | 948 independent reflections |
Radiation source: fine-focus sealed tube | 877 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 8.3 pixels mm-1 | θmax = 27.1°, θmin = 3.1° |
Sets of exposures each taken over 0.3° ω rotation scans | h = −8→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −9→11 |
Tmin = 0.773, Tmax = 0.930 | l = −9→8 |
2491 measured reflections |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | Only H-atom coordinates refined |
S = 1.06 | w = 1/[σ2(Fo2) + (0.067P)2 + 0.3254P] where P = (Fo2 + 2Fc2)/3 |
948 reflections | (Δ/σ)max = 0.024 |
79 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Special details top
Refinement. Data were collected by measuring three sets of exposures with the detector set at 2θ = 29°, crystal-to-detector distance 5.00 cm. Refinement of F2 against ALL reflections. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.35356 (17) | 0.51992 (13) | 0.72550 (19) | 0.0235 (3) | |
O2 | 0.36045 (17) | 0.73594 (13) | 0.87769 (19) | 0.0222 (3) | |
H2 | 0.216 (4) | 0.701 (3) | 0.853 (4) | 0.033* | |
O3 | 1.01208 (17) | 0.68937 (14) | 0.8410 (2) | 0.0252 (3) | |
N1 | 0.7322 (2) | 0.55858 (16) | 0.7632 (2) | 0.0198 (3) | |
H1 | 0.668 (3) | 0.479 (2) | 0.718 (3) | 0.024* | |
C1 | 0.4401 (2) | 0.63051 (17) | 0.8118 (2) | 0.0172 (4) | |
C2 | 0.6557 (2) | 0.66295 (17) | 0.8631 (2) | 0.0181 (4) | |
H21 | 0.671 (3) | 0.757 (2) | 0.821 (3) | 0.022* | |
H22 | 0.731 (3) | 0.656 (2) | 1.012 (3) | 0.022* | |
C3 | 0.9077 (2) | 0.57947 (18) | 0.7613 (2) | 0.0197 (4) | |
H31 | 0.947 (3) | 0.504 (2) | 0.695 (3) | 0.024* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0162 (6) | 0.0234 (6) | 0.0307 (7) | −0.0036 (4) | 0.0103 (5) | −0.0039 (5) |
O2 | 0.0141 (6) | 0.0242 (6) | 0.0313 (7) | −0.0016 (4) | 0.0128 (5) | −0.0037 (5) |
O3 | 0.0130 (6) | 0.0319 (7) | 0.0329 (7) | −0.0010 (5) | 0.0123 (5) | −0.0006 (5) |
N1 | 0.0141 (6) | 0.0210 (7) | 0.0256 (7) | 0.0000 (5) | 0.0100 (5) | −0.0020 (5) |
C1 | 0.0125 (7) | 0.0207 (7) | 0.0185 (7) | 0.0002 (5) | 0.0071 (6) | 0.0029 (6) |
C2 | 0.0131 (7) | 0.0209 (8) | 0.0214 (8) | 0.0000 (6) | 0.0085 (6) | −0.0012 (6) |
C3 | 0.0126 (7) | 0.0263 (8) | 0.0200 (7) | 0.0046 (6) | 0.0069 (6) | 0.0029 (6) |
Geometric parameters (Å, º) top
O1—C1 | 1.2113 (19) | N1—H1 | 0.85 (2) |
O2—C1 | 1.3229 (19) | C1—C2 | 1.508 (2) |
O2—H2 | 1.06 (2) | C2—H21 | 0.93 (2) |
O3—C3 | 1.244 (2) | C2—H22 | 0.95 (2) |
N1—C3 | 1.326 (2) | C3—H31 | 0.95 (2) |
N1—C2 | 1.449 (2) | ||
C1—O2—H2 | 107.6 (13) | N1—C2—H21 | 108.7 (12) |
C3—N1—C2 | 120.81 (14) | C1—C2—H21 | 112.0 (13) |
C3—N1—H1 | 120.4 (15) | N1—C2—H22 | 109.2 (12) |
C2—N1—H1 | 118.4 (15) | C1—C2—H22 | 107.1 (12) |
O1—C1—O2 | 124.68 (14) | H21—C2—H22 | 108.7 (18) |
O1—C1—C2 | 123.83 (14) | O3—C3—N1 | 122.05 (15) |
O2—C1—C2 | 111.46 (13) | O3—C3—H31 | 123.3 (13) |
N1—C2—C1 | 110.98 (13) | N1—C3—H31 | 114.7 (13) |
O1—C1—C2—N1 | 10.2 (2) | C2—N1—C3—O3 | −1.2 (2) |
C1—C2—N1—C3 | 169.77 (14) | O2—C1—C2—N1 | −171.36 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.85 (2) | 2.31 (2) | 3.100 (2) | 154 (2) |
O2—H2···O3ii | 1.06 (2) | 1.48 (2) | 2.5229 (16) | 165 (2) |
C2—H21···O1iii | 0.93 (2) | 2.43 (2) | 3.327 (2) | 160.9 (17) |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x−1, y, z; (iii) −x+1, y+1/2, −z+3/2. |