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In the title adduct, C9H11NO2·C4H4O4, the amino acid mol­ecules exist as zwitterions and the fumaric acid mol­ecules exist in the unionized state, a feature uncommon in similar crystal structures. The asymmetric unit is composed of two mol­ecules of each species. The fumaric acid mol­ecules are related to each other through a pseudo-inversion centre and are essentially planar. The phenyl­alanine and fumaric acid mol­ecules form hydrogen-bonded double layers, linked together by hydrogen bonds and extending along [001]. These double layers are flanked, on either side, by the hydro­phobic side chains of phenyl­alanine, leading to alternating hydro­philic and hydro­phobic zones.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803011942/wn6164sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803011942/wn6164Isup2.hkl
Contains datablock I

CCDC reference: 217455

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.032
  • wR factor = 0.085
  • Data-to-parameter ratio = 6.6

checkCIF results

No syntax errors found


Amber Alert Alert Level B:
PLAT_111 Alert B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 95 PerFit PLAT_113 Alert B ADDSYM Suggests Possible Pseudo/New Spacegroup . P-1
Yellow Alert Alert Level C:
REFNR_01 Alert C Ratio of reflections to parameters is < 8 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda 0.5942 Proportion of unique data used 0.9488 Ratio reflections to parameters 6.5847 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 24.98 From the CIF: _reflns_number_total 2540 Count of symmetry unique reflns 2417 Completeness (_total/calc) 105.09% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 123 Fraction of Friedel pairs measured 0.051 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.
0 Alert Level A = Potentially serious problem
2 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

In view of the importance of non-covalent interactions in the aggregation and interaction patterns of biological molecules, we have been elucidating the X-ray crystal structures of simple complexes involving amino acids and dicarboxylic acids. Precise crystallographic data on such complexes are expected to provide useful insights into chemical evolution and self-assembly, processes that might have led to the emergence of primitive multi-molecular systems. Fumaric acid (trans-butenedioic acid) is among the organic compounds widely found in Nature, and is a key intermediate in the biosynthesis of organic acids. X-ray investigations of amino acid complexes with fumaric acid seem to have been first initiated in our laboratory. Such investigations have provided some interesting data regarding the ionization states and stoichiometry of these molecules. Recently, we have reported the crystal structures of complexes of maleic acid (cis-butenedioic acid) with DL-phenylalanine (Alagar, Subha Nandhini et al., 2003) and L-phenylalanine (Alagar et al., 2001). The present study reports the crystal structure of a complex of L-phenylalanine with fumaric acid.

Fig.1 shows the molecular structure of (I) with the atom-numbering scheme. There are two molecules of phenylalanine and two molecules of fumaric acid in the asymmetric unit. The ionization state exhibited in this structure is uncommon in similar crystal structures. The amino acid molecules exist as zwitterions and the two fumaric acid molecules exist in the unionized state. Usually, in the crystal structures of amino acid-carboyxlic acid complexes, the amino acid molecules prefer the cationic state and the carboxylic acids the anionic state, either as carboxylate(2-) or semicarboxylate(1-) anions. The two fumaric acid molecules in the asymmetric unit are related to each other through a psuedo-inversion centre, and are essentially planar.

Interestingly, if we exclude the N and O atoms, then the two independent amino acid molecules are also related by a pseudo-inversion centre. This is evident from the torsion angles ψ1[−164.1 (2), −138.6 (3)°], ψ2[17.8 (4), 41.1 (3)°], χ1[−69.4 (3), 166.3 (3)°], χ21[−96.9 (4), 99.2 (4)°], χ22[83.2 (4), −79.1 (4)].

The phenylalanine and fumaric acid molecules form hydrogen-bonded double layers, linked together by N—H···O and O—H···O hydrogen bonds, and extending along [001]. These double layers are flanked, on either side, by the hydrophobic side chains of phenylalanine, leading to alternating hydrophilic and hydrophobic zones (Fig.2). In addition to van der Waals interactions, a short carbonyl contact C1'···O2 (x + 1, y, z − 1) = 2.998 (3) Å is also observed (Allen et al., 1998).

In the present structure there are no direct hydrogen-bonded interactions between the fumaric acid molecules. This situation is also observed for the non-amino-acid components of the following complexes: L-phenylalanine L-phenylalaninium formate (Görbitz & Etter, 1992), L-phenylalaninium maleate (Alagar et al., 2001), DL-phenylalaninium maleate (Alagar, Subha Nandhini et al.,2003), DL– valine fumaric acid 2/1 (Alagar, Krishnakumar et al., 2003), and DL-valinium maleate (Alagar et al., 2001).

Experimental top

Colourless, single crystals of (I) were grown as transparent prisms, from a saturated aqueous solution containing L-phenylalanine and fumaric acid in a 1:1 stoichiometric ratio.

Refinement top

The absolute configuation of L-phenylalanine fumaric acid was not established by the analysis but is known from the configuration of the starting reagents. The H atoms were placed at calculated positions and were allowed to ride on their respective parent atoms, with C—H = 0.96 Å, N—H = 0.89 Å, O—H = 0.82 Å and Uiso = 0.05 Å2.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom-numbering scheme and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the molecules of (I), viewed down the a axis.
(I) top
Crystal data top
C9H11NO2·C4H4O4Z = 2
Mr = 281.26F(000) = 296
Triclinic, P1Dx = 1.361 Mg m3
Dm = 1.35 (2) Mg m3
Dm measured by flotation in a mixture of xylene and bromoform
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.7016 (10) ÅCell parameters from 25 reflections
b = 11.4864 (15) Åθ = 2–7°
c = 11.5542 (17) ŵ = 0.11 mm1
α = 67.953 (11)°T = 293 K
β = 81.158 (13)°Prism, colorless
γ = 79.379 (15)°0.28 × 0.23 × 0.18 mm
V = 686.37 (19) Å3
Data collection top
Enraf Nonius CAD4
diffractometer
2154 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.013
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
non–profiled ω/2θ scansh = 66
Absorption correction: ψ scan
[North et al., 1968]
k = 013
Tmin = 0.960, Tmax = 0.975l = 1213
2541 measured reflections2 standard reflections every 100 reflections
2540 independent reflections intensity decay: <1%
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0551P)2 + 0.0393P]
where P = (Fo2 + 2Fc2)/3
2410 reflections(Δ/σ)max < 0.001
366 parametersΔρmax = 0.18 e Å3
3 restraintsΔρmin = 0.14 e Å3
Crystal data top
C9H11NO2·C4H4O4γ = 79.379 (15)°
Mr = 281.26V = 686.37 (19) Å3
Triclinic, P1Z = 2
a = 5.7016 (10) ÅMo Kα radiation
b = 11.4864 (15) ŵ = 0.11 mm1
c = 11.5542 (17) ÅT = 293 K
α = 67.953 (11)°0.28 × 0.23 × 0.18 mm
β = 81.158 (13)°
Data collection top
Enraf Nonius CAD4
diffractometer
2154 reflections with I > 2σ(I)
Absorption correction: ψ scan
[North et al., 1968]
Rint = 0.013
Tmin = 0.960, Tmax = 0.9752 standard reflections every 100 reflections
2541 measured reflections intensity decay: <1%
2540 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0323 restraints
wR(F2) = 0.085H-atom parameters constrained
S = 1.03Δρmax = 0.18 e Å3
2410 reflectionsΔρmin = 0.14 e Å3
366 parameters
Special details top

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
xyzUiso*/Ueq
O11.2177 (3)0.5907 (2)0.15771 (18)0.0444 (6)
O21.0094 (3)0.64490 (19)0.31153 (16)0.0334 (4)
O30.8382 (4)0.5849 (2)0.54851 (19)0.0491 (6)
H30.88060.59600.47450.074*
O40.4730 (4)0.6316 (2)0.48204 (18)0.0435 (5)
O50.3373 (4)0.5769 (3)0.9349 (2)0.0646 (8)
H50.27630.59190.99780.097*
O60.0355 (4)0.6312 (3)0.8789 (2)0.0744 (9)
O1'0.2517 (3)0.08448 (19)0.13858 (17)0.0387 (5)
O2'0.3549 (3)0.0946 (2)0.33444 (18)0.0435 (5)
O3'0.0096 (4)0.9407 (3)0.9166 (2)0.0583 (7)
H3'0.06190.93220.98910.087*
O4'0.3397 (4)0.8650 (2)0.99990 (19)0.0576 (7)
O5'0.5047 (4)0.9449 (3)0.5405 (2)0.0668 (8)
H5'0.57390.95060.47130.100*
O6'0.8757 (4)0.8889 (3)0.5960 (2)0.0570 (7)
N10.5858 (4)0.6716 (2)0.21939 (19)0.0316 (5)
H1A0.45550.66520.18970.047*
H1B0.60130.75310.19710.047*
H1C0.57210.63600.30270.047*
N1'0.1311 (4)0.1469 (2)0.3734 (2)0.0367 (5)
H1'10.27880.13480.37770.055*
H1'20.13120.22740.38250.055*
H1'30.03280.12910.43410.055*
C11.0254 (5)0.6161 (3)0.2165 (2)0.0297 (6)
C20.8006 (4)0.6057 (3)0.1671 (2)0.0309 (6)
H20.81550.64900.07580.037*
C30.7768 (5)0.4663 (3)0.1947 (3)0.0431 (7)
H3A0.62630.46340.16720.052*
H3B0.90490.43270.14530.052*
C40.7852 (6)0.3813 (3)0.3305 (3)0.0469 (8)
C50.9960 (7)0.3078 (4)0.3747 (4)0.0651 (11)
H5A1.13470.31120.32000.078*
C61.0033 (10)0.2292 (4)0.4992 (5)0.0872 (16)
H61.14630.17930.52690.105*
C70.8036 (12)0.2240 (5)0.5817 (5)0.0909 (16)
H70.81000.17180.66550.109*
C80.5908 (10)0.2975 (5)0.5391 (4)0.0829 (13)
H80.45360.29500.59460.100*
C90.5819 (7)0.3741 (4)0.4150 (4)0.0622 (10)
H90.43740.42190.38720.075*
C100.6026 (5)0.6082 (3)0.5643 (3)0.0359 (7)
C110.5129 (5)0.6016 (3)0.6938 (2)0.0377 (7)
H110.62040.59280.75040.045*
C120.2810 (5)0.6082 (3)0.7287 (3)0.0411 (7)
H120.17750.61390.67130.049*
C130.1762 (6)0.6070 (3)0.8556 (3)0.0444 (8)
C1'0.2059 (5)0.0818 (3)0.2398 (2)0.0307 (6)
C2'0.0482 (5)0.0623 (3)0.2493 (2)0.0321 (6)
H2'0.15590.08470.18380.039*
C3'0.0625 (6)0.0752 (3)0.2302 (3)0.0455 (8)
H3'10.06410.10370.28390.055*
H3'20.21480.08020.25450.055*
C4'0.0386 (6)0.1612 (3)0.0959 (3)0.0475 (8)
C5'0.1791 (7)0.2338 (3)0.0585 (4)0.0628 (10)
H5'10.31090.23180.11730.075*
C6'0.1996 (10)0.3090 (4)0.0661 (6)0.0899 (17)
H6'0.34590.35670.09080.108*
C7'0.0076 (12)0.3139 (4)0.1529 (5)0.0903 (17)
H7'0.02280.36520.23640.108*
C8'0.2109 (10)0.2424 (5)0.1171 (4)0.0885 (15)
H8'0.34240.24550.17630.106*
C9'0.2316 (8)0.1668 (4)0.0068 (4)0.0662 (10)
H9'0.37800.11870.03080.079*
C10'0.2233 (6)0.9046 (3)0.9116 (3)0.0411 (7)
C11'0.3249 (6)0.9177 (3)0.7809 (3)0.0432 (7)
H11'0.22070.93690.71980.052*
C12'0.5558 (6)0.9031 (3)0.7497 (3)0.0461 (8)
H12'0.65830.88670.81100.055*
C13'0.6629 (6)0.9112 (3)0.6226 (3)0.0415 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0214 (10)0.0850 (16)0.0390 (11)0.0062 (10)0.0017 (8)0.0384 (11)
O20.0288 (10)0.0518 (12)0.0259 (9)0.0084 (8)0.0007 (7)0.0203 (9)
O30.0349 (12)0.0846 (17)0.0295 (10)0.0066 (11)0.0023 (9)0.0248 (12)
O40.0383 (11)0.0658 (14)0.0257 (10)0.0002 (10)0.0044 (9)0.0185 (9)
O50.0410 (13)0.125 (2)0.0379 (13)0.0009 (14)0.0006 (10)0.0463 (15)
O60.0396 (15)0.136 (3)0.0395 (13)0.0061 (15)0.0027 (10)0.0331 (15)
O1'0.0364 (11)0.0551 (12)0.0281 (10)0.0076 (9)0.0051 (8)0.0174 (9)
O2'0.0308 (11)0.0737 (14)0.0320 (11)0.0111 (10)0.0006 (8)0.0252 (10)
O3'0.0423 (13)0.107 (2)0.0307 (11)0.0080 (13)0.0003 (9)0.0326 (13)
O4'0.0548 (15)0.0835 (18)0.0320 (12)0.0068 (13)0.0071 (10)0.0243 (12)
O5'0.0401 (13)0.128 (2)0.0357 (12)0.0035 (14)0.0003 (10)0.0382 (15)
O6'0.0384 (14)0.0931 (19)0.0406 (13)0.0020 (12)0.0008 (10)0.0315 (13)
N10.0207 (10)0.0502 (13)0.0267 (11)0.0040 (9)0.0010 (8)0.0180 (10)
N1'0.0291 (12)0.0482 (14)0.0327 (12)0.0009 (10)0.0048 (10)0.0155 (11)
C10.0270 (14)0.0392 (15)0.0239 (12)0.0039 (11)0.0022 (10)0.0128 (11)
C20.0224 (12)0.0495 (16)0.0241 (12)0.0054 (11)0.0004 (10)0.0173 (12)
C30.0304 (15)0.059 (2)0.0532 (18)0.0069 (14)0.0043 (13)0.0345 (16)
C40.0449 (18)0.0426 (18)0.063 (2)0.0090 (14)0.0119 (15)0.0262 (16)
C50.058 (2)0.049 (2)0.091 (3)0.0016 (18)0.023 (2)0.024 (2)
C60.094 (4)0.050 (3)0.110 (4)0.002 (2)0.049 (3)0.008 (3)
C70.126 (5)0.068 (3)0.074 (3)0.035 (3)0.035 (3)0.001 (2)
C80.092 (3)0.083 (3)0.065 (3)0.029 (3)0.002 (2)0.010 (2)
C90.054 (2)0.065 (2)0.061 (2)0.0142 (18)0.0051 (18)0.0135 (19)
C100.0363 (16)0.0427 (17)0.0263 (14)0.0044 (13)0.0005 (12)0.0112 (12)
C110.0416 (17)0.0505 (18)0.0211 (13)0.0048 (14)0.0025 (12)0.0138 (13)
C120.0396 (18)0.0572 (19)0.0276 (14)0.0042 (14)0.0020 (12)0.0181 (14)
C130.0399 (18)0.063 (2)0.0295 (15)0.0041 (14)0.0005 (13)0.0186 (14)
C1'0.0300 (14)0.0339 (15)0.0294 (14)0.0032 (12)0.0043 (11)0.0126 (11)
C2'0.0314 (14)0.0401 (15)0.0264 (13)0.0050 (11)0.0011 (10)0.0143 (11)
C3'0.0489 (18)0.0450 (18)0.0489 (18)0.0091 (14)0.0125 (14)0.0195 (15)
C4'0.0521 (19)0.0384 (17)0.055 (2)0.0104 (14)0.0132 (15)0.0148 (15)
C5'0.061 (2)0.042 (2)0.081 (3)0.0008 (17)0.017 (2)0.0161 (19)
C6'0.093 (4)0.053 (3)0.108 (4)0.005 (2)0.054 (3)0.003 (3)
C7'0.128 (5)0.066 (3)0.062 (3)0.027 (3)0.038 (3)0.011 (2)
C8'0.111 (4)0.083 (3)0.057 (3)0.035 (3)0.002 (3)0.001 (2)
C9'0.059 (2)0.071 (3)0.058 (2)0.0121 (19)0.0060 (18)0.0087 (19)
C10'0.0461 (18)0.0507 (19)0.0316 (16)0.0065 (14)0.0020 (14)0.0210 (14)
C11'0.0444 (19)0.057 (2)0.0303 (15)0.0056 (14)0.0051 (13)0.0183 (14)
C12'0.046 (2)0.067 (2)0.0307 (15)0.0052 (16)0.0036 (13)0.0243 (15)
C13'0.0410 (18)0.0550 (19)0.0321 (15)0.0051 (14)0.0044 (12)0.0198 (14)
Geometric parameters (Å, º) top
O1—C11.245 (3)C4—C91.390 (5)
O2—C11.247 (3)C5—C61.384 (7)
N1—C21.488 (3)C5—H5A0.9300
C1—C21.521 (3)C6—C71.363 (8)
C2—C31.539 (4)C6—H60.9300
C3—C41.508 (5)C7—C81.386 (8)
O3—C101.318 (4)C7—H70.9300
O3—H30.8200C8—C91.375 (6)
O4—C101.214 (4)C8—H80.9300
O5—C131.307 (4)C9—H90.9300
O5—H50.8200C10—C111.483 (4)
O6—C131.200 (4)C11—C121.319 (4)
O1'—C1'1.249 (3)C11—H110.9300
O2'—C1'1.257 (3)C12—C131.491 (4)
N1'—C2'1.488 (3)C12—H120.9300
C1'—C2'1.533 (4)C2'—H2'0.9800
C2'—C3'1.526 (4)C3'—H3'10.9700
C3'—C4'1.506 (4)C3'—H3'20.9700
O3'—C10'1.315 (4)C4'—C9'1.379 (5)
O3'—H3'0.8200C4'—C5'1.391 (5)
O4'—C10'1.199 (4)C5'—C6'1.384 (7)
O5'—C13'1.313 (4)C5'—H5'10.9300
O5'—H5'0.8200C6'—C7'1.360 (8)
O6'—C13'1.209 (4)C6'—H6'0.9300
N1—H1A0.8900C7'—C8'1.387 (8)
N1—H1B0.8900C7'—H7'0.9300
N1—H1C0.8900C8'—C9'1.379 (6)
N1'—H1'10.8900C8'—H8'0.9300
N1'—H1'20.8900C9'—H9'0.9300
N1'—H1'30.8900C10'—C11'1.493 (4)
C2—H20.9800C11'—C12'1.307 (5)
C3—H3A0.9700C11'—H11'0.9300
C3—H3B0.9700C12'—C13'1.477 (4)
C4—C51.381 (5)C12'—H12'0.9300
C10—O3—H3109.5C12—C11—H11119.9
C13—O5—H5109.5C10—C11—H11119.9
C10'—O3'—H3'109.5C11—C12—C13123.3 (3)
C13'—O5'—H5'109.5C11—C12—H12118.3
C2—N1—H1A109.5C13—C12—H12118.3
C2—N1—H1B109.5O6—C13—O5125.2 (3)
H1A—N1—H1B109.5O6—C13—C12121.7 (3)
C2—N1—H1C109.5O5—C13—C12113.1 (3)
H1A—N1—H1C109.5O1'—C1'—O2'124.1 (3)
H1B—N1—H1C109.5O1'—C1'—C2'118.0 (2)
C2'—N1'—H1'1109.5O2'—C1'—C2'117.9 (2)
C2'—N1'—H1'2109.5N1'—C2'—C1'110.4 (2)
H1'1—N1'—H1'2109.5N1'—C2'—C3'109.5 (2)
C2'—N1'—H1'3109.5C1'—C2'—C3'111.8 (2)
H1'1—N1'—H1'3109.5N1'—C2'—H2'108.4
H1'2—N1'—H1'3109.5C3'—C2'—H2'108.4
O1—C1—O2124.6 (2)C1'—C2'—H2'108.4
O1—C1—C2115.2 (2)C4'—C3'—C2'111.7 (2)
O2—C1—C2120.2 (2)C4'—C3'—H3'1109.3
N1—C2—C1110.2 (2)C2'—C3'—H3'1109.3
N1—C2—C3112.0 (2)C4'—C3'—H3'2109.3
C1—C2—C3111.1 (2)C2'—C3'—H3'2109.3
N1—C2—H2107.8H3'1—C3'—H3'2107.9
C1—C2—H2107.8C9'—C4'—C5'118.8 (3)
C3—C2—H2107.8C9'—C4'—C3'120.3 (3)
C4—C3—C2114.9 (2)C5'—C4'—C3'120.9 (3)
C4—C3—H3A108.5C6'—C5'—C4'120.0 (4)
C2—C3—H3A108.5C6'—C5'—H5'1120.0
C4—C3—H3B108.5C4'—C5'—H5'1120.0
C2—C3—H3B108.5C7'—C6'—C5'120.6 (4)
H3A—C3—H3B107.5C7'—C6'—H6'119.7
C5—C4—C9117.9 (4)C5'—C6'—H6'119.7
C5—C4—C3120.8 (3)C6'—C7'—C8'120.1 (4)
C9—C4—C3121.2 (3)C6'—C7'—H7'120.0
C4—C5—C6120.8 (4)C8'—C7'—H7'120.0
C4—C5—H5A119.6C9'—C8'—C7'119.5 (5)
C6—C5—H5A119.6C9'—C8'—H8'120.2
C7—C6—C5120.8 (4)C7'—C8'—H8'120.2
C7—C6—H6119.6C8'—C9'—C4'121.0 (4)
C5—C6—H6119.6C8'—C9'—H9'119.5
C6—C7—C8119.1 (5)C4'—C9'—H9'119.5
C6—C7—H7120.4O4'—C10'—O3'124.9 (3)
C8—C7—H7120.4O4'—C10'—C11'124.1 (3)
C9—C8—C7120.3 (5)O3'—C10'—C11'111.0 (3)
C9—C8—H8119.9C12'—C11'—C10'122.1 (3)
C7—C8—H8119.9C12'—C11'—H11'119.0
C8—C9—C4121.1 (4)C10'—C11'—H11'119.0
C8—C9—H9119.5C11'—C12'—C13'123.6 (3)
C4—C9—H9119.5C11'—C12'—H12'118.2
O4—C10—O3123.6 (3)C13'—C12'—H12'118.2
O4—C10—C11123.6 (3)O6'—C13'—O5'122.8 (3)
O3—C10—C11112.7 (2)O6'—C13'—C12'123.6 (3)
C12—C11—C10120.1 (3)O5'—C13'—C12'113.6 (3)
O1—C1—C2—N1164.1 (2)O1'—C1'—C2'—N1'138.6 (2)
O2—C1—C2—N117.8 (4)O2'—C1'—C2'—N1'41.1 (3)
O1—C1—C2—C371.2 (3)O1'—C1'—C2'—C3'99.3 (3)
O2—C1—C2—C3106.9 (3)O2'—C1'—C2'—C3'81.0 (3)
N1—C2—C3—C469.4 (3)N1'—C2'—C3'—C4'166.3 (2)
C1—C2—C3—C454.3 (3)C1'—C2'—C3'—C4'71.1 (3)
C2—C3—C4—C596.9 (4)C2'—C3'—C4'—C5'99.2 (4)
C2—C3—C4—C983.2 (4)C2'—C3'—C4'—C9'79.1 (4)
C9—C4—C5—C60.3 (6)C9'—C4'—C5'—C6'0.5 (6)
C3—C4—C5—C6179.6 (4)C3'—C4'—C5'—C6'177.8 (4)
C4—C5—C6—C71.1 (7)C4'—C5'—C6'—C7'0.6 (7)
C5—C6—C7—C80.8 (8)C5'—C6'—C7'—C8'0.4 (8)
C6—C7—C8—C90.3 (8)C6'—C7'—C8'—C9'0.0 (8)
C7—C8—C9—C41.1 (7)C7'—C8'—C9'—C4'0.1 (7)
C5—C4—C9—C80.8 (6)C5'—C4'—C9'—C8'0.1 (6)
C3—C4—C9—C8179.3 (4)C3'—C4'—C9'—C8'178.2 (4)
O4—C10—C11—C127.2 (5)O4'—C10'—C11'—C12'9.7 (5)
O3—C10—C11—C12172.2 (3)O3'—C10'—C11'—C12'171.1 (3)
C10—C11—C12—C13177.7 (3)C10'—C11'—C12'—C13'177.9 (3)
C11—C12—C13—O6169.1 (4)C11'—C12'—C13'—O6'174.6 (4)
C11—C12—C13—O511.1 (5)C11'—C12'—C13'—O5'5.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.821.832.633 (3)168
O5—H5···O1i0.821.822.616 (3)163
O3—H3···O1ii0.821.862.659 (3)166
O5—H5···O2iii0.821.812.570 (3)154
N1—H1A···O1iv0.891.882.730 (3)160
N1—H1B···O1iii0.892.022.882 (3)162
N1—H1C···O40.892.052.880 (3)156
N1—H11···O2v0.892.163.032 (3)165
N1—H12···O2vi0.892.182.959 (3)146
N1—H12···O4vii0.892.422.894 (3)113
N1—H13···O6vi0.892.012.886 (3)166
Symmetry codes: (i) x1, y, z+1; (ii) x, y+1, z+1; (iii) x+1, y+1, z; (iv) x1, y, z; (v) x+1, y, z; (vi) x1, y1, z; (vii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC9H11NO2·C4H4O4
Mr281.26
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)5.7016 (10), 11.4864 (15), 11.5542 (17)
α, β, γ (°)67.953 (11), 81.158 (13), 79.379 (15)
V3)686.37 (19)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.28 × 0.23 × 0.18
Data collection
DiffractometerEnraf Nonius CAD4
diffractometer
Absorption correctionψ scan
[North et al., 1968]
Tmin, Tmax0.960, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections
2541, 2540, 2154
Rint0.013
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.085, 1.03
No. of reflections2410
No. of parameters366
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.14

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1999), SHELXL97.

Selected geometric parameters (Å, º) top
O1—C11.245 (3)O1'—C1'1.249 (3)
O2—C11.247 (3)O2'—C1'1.257 (3)
N1—C21.488 (3)N1'—C2'1.488 (3)
C1—C21.521 (3)C1'—C2'1.533 (4)
C2—C31.539 (4)C2'—C3'1.526 (4)
C3—C41.508 (5)C3'—C4'1.506 (4)
O3—C101.318 (4)O3'—C10'1.315 (4)
O4—C101.214 (4)O4'—C10'1.199 (4)
O5—C131.307 (4)O5'—C13'1.313 (4)
O6—C131.200 (4)O6'—C13'1.209 (4)
O1—C1—O2124.6 (2)O1'—C1'—O2'124.1 (3)
N1—C2—C1110.2 (2)N1'—C2'—C1'110.4 (2)
N1—C2—C3112.0 (2)N1'—C2'—C3'109.5 (2)
C1—C2—C3111.1 (2)C1'—C2'—C3'111.8 (2)
O4—C10—O3123.6 (3)O4'—C10'—O3'124.9 (3)
C12—C11—C10120.1 (3)C12'—C11'—C10'122.1 (3)
O6—C13—O5125.2 (3)O6'—C13'—O5'122.8 (3)
O1—C1—C2—N1164.1 (2)O1'—C1'—C2'—N1'138.6 (2)
O2—C1—C2—N117.8 (4)O2'—C1'—C2'—N1'41.1 (3)
O1—C1—C2—C371.2 (3)O1'—C1'—C2'—C3'99.3 (3)
O2—C1—C2—C3106.9 (3)O2'—C1'—C2'—C3'81.0 (3)
N1—C2—C3—C469.4 (3)N1'—C2'—C3'—C4'166.3 (2)
C1—C2—C3—C454.3 (3)C1'—C2'—C3'—C4'71.1 (3)
C2—C3—C4—C596.9 (4)C2'—C3'—C4'—C5'99.2 (4)
C2—C3—C4—C983.2 (4)C2'—C3'—C4'—C9'79.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.821.832.633 (3)168
O5—H5···O1i0.821.822.616 (3)163
O3'—H3'···O1'ii0.821.862.659 (3)166
O5'—H5'···O2'iii0.821.812.570 (3)154
N1—H1A···O1iv0.891.882.730 (3)160
N1—H1B···O1'iii0.892.022.882 (3)162
N1—H1C···O40.892.052.880 (3)156
N1'—H1'1···O2'v0.892.163.032 (3)165
N1'—H1'2···O2vi0.892.182.959 (3)146
N1'—H1'2···O4vii0.892.422.894 (3)113
N1'—H1'3···O6'vi0.892.012.886 (3)166
Symmetry codes: (i) x1, y, z+1; (ii) x, y+1, z+1; (iii) x+1, y+1, z; (iv) x1, y, z; (v) x+1, y, z; (vi) x1, y1, z; (vii) x, y1, z.
 

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