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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—H...O hydrogen bond with the OH group of the carboxyl­ic acid function as the acceptor.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804009122/bt6447sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804009122/bt6447Isup2.hkl
Contains datablock I

CCDC reference: 239274

Key indicators

  • Single-crystal X-ray study
  • T = 105 K
  • Mean [sigma](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
C3H5NO3F(000) = 216
Mr = 103.08Dx = 1.579 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.4378 (15) ÅCell parameters from 1914 reflections
b = 9.1650 (19) Åθ = 3.1–27.1°
c = 7.1002 (14) ŵ = 0.14 mm1
β = 116.348 (3)°T = 105 K
V = 433.72 (15) Å3Block, colourless
Z = 41.10 × 0.85 × 0.50 mm
Data collection top
Siemens SMART CCD
diffractometer
948 independent reflections
Radiation source: fine-focus sealed tube877 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 8.3 pixels mm-1θmax = 27.1°, θmin = 3.1°
Sets of exposures each taken over 0.3° ω rotation scansh = 89
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 911
Tmin = 0.773, Tmax = 0.930l = 98
2491 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122Only 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 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.27 e Å3
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
xyzUiso*/Ueq
O10.35356 (17)0.51992 (13)0.72550 (19)0.0235 (3)
O20.36045 (17)0.73594 (13)0.87769 (19)0.0222 (3)
H20.216 (4)0.701 (3)0.853 (4)0.033*
O31.01208 (17)0.68937 (14)0.8410 (2)0.0252 (3)
N10.7322 (2)0.55858 (16)0.7632 (2)0.0198 (3)
H10.668 (3)0.479 (2)0.718 (3)0.024*
C10.4401 (2)0.63051 (17)0.8118 (2)0.0172 (4)
C20.6557 (2)0.66295 (17)0.8631 (2)0.0181 (4)
H210.671 (3)0.757 (2)0.821 (3)0.022*
H220.731 (3)0.656 (2)1.012 (3)0.022*
C30.9077 (2)0.57947 (18)0.7613 (2)0.0197 (4)
H310.947 (3)0.504 (2)0.695 (3)0.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0162 (6)0.0234 (6)0.0307 (7)0.0036 (4)0.0103 (5)0.0039 (5)
O20.0141 (6)0.0242 (6)0.0313 (7)0.0016 (4)0.0128 (5)0.0037 (5)
O30.0130 (6)0.0319 (7)0.0329 (7)0.0010 (5)0.0123 (5)0.0006 (5)
N10.0141 (6)0.0210 (7)0.0256 (7)0.0000 (5)0.0100 (5)0.0020 (5)
C10.0125 (7)0.0207 (7)0.0185 (7)0.0002 (5)0.0071 (6)0.0029 (6)
C20.0131 (7)0.0209 (8)0.0214 (8)0.0000 (6)0.0085 (6)0.0012 (6)
C30.0126 (7)0.0263 (8)0.0200 (7)0.0046 (6)0.0069 (6)0.0029 (6)
Geometric parameters (Å, º) top
O1—C11.2113 (19)N1—H10.85 (2)
O2—C11.3229 (19)C1—C21.508 (2)
O2—H21.06 (2)C2—H210.93 (2)
O3—C31.244 (2)C2—H220.95 (2)
N1—C31.326 (2)C3—H310.95 (2)
N1—C21.449 (2)
C1—O2—H2107.6 (13)N1—C2—H21108.7 (12)
C3—N1—C2120.81 (14)C1—C2—H21112.0 (13)
C3—N1—H1120.4 (15)N1—C2—H22109.2 (12)
C2—N1—H1118.4 (15)C1—C2—H22107.1 (12)
O1—C1—O2124.68 (14)H21—C2—H22108.7 (18)
O1—C1—C2123.83 (14)O3—C3—N1122.05 (15)
O2—C1—C2111.46 (13)O3—C3—H31123.3 (13)
N1—C2—C1110.98 (13)N1—C3—H31114.7 (13)
O1—C1—C2—N110.2 (2)C2—N1—C3—O31.2 (2)
C1—C2—N1—C3169.77 (14)O2—C1—C2—N1171.36 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.85 (2)2.31 (2)3.100 (2)154 (2)
O2—H2···O3ii1.06 (2)1.48 (2)2.5229 (16)165 (2)
C2—H21···O1iii0.93 (2)2.43 (2)3.327 (2)160.9 (17)
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x1, y, z; (iii) x+1, y+1/2, z+3/2.
 

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