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The title compound, C15H12N2O4, displays a twisted conformation as reflected in the dihedral angle between the aromatic rings of 59.77 (7)°. Intra- and inter­molecular O—H...O inter­actions are found, with the latter leading to a double chain arranged about a zigzag chain of {O—H...O}n inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031327/hg2251sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031327/hg2251Isup2.hkl
Contains datablock I

CCDC reference: 657652

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.046
  • wR factor = 0.129
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.878 1.000 Tmin(prime) and Tmax expected: 0.968 0.987 RR(prime) = 0.895 Please check that your absorption correction is appropriate. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.89 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT432_ALERT_2_C Short Inter X...Y Contact C8 .. C12' .. 3.19 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. N2 .. 2.66 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. O2 .. 2.84 Ang.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The synthesis of the title compound (I) and their interactions with triorganotin(IV) moieties, have attracted much interest owing to their novel structural possibilities (Basu Baul et al., 1996, 2006), and their significant biological activity towards mosquito larvae (Basu Baul et al., 2004) and sea urchin early development stages (Basu Baul et al., 2006).

Compound (I), Fig. 1, assumes an E-conformation. There is a twist in the molecule as seen in the N1—N2—C8—C9 and, in particular, the N2—N1—C7—C2 torsion angles of -163.77 (13) and -141.01 (14)°, respectively. This is also reflected in the dihedral angle of 59.77 (7)° formed between the C2—C7 and C8—C13 aromatic rings.

The hydroxyl group participates in an intramolecular O3—H···O4 hydrogen-bond and at the same time forms an intermolecular O3—H···O3 interaction with a centrosymmetric mate, Table 1, to form a double chain, Fig. 2. Additional stabilization to the chain are afforded by C—H···O1 contacts. Further, this arrangement allows for the close approach of the C=O4 carbonyl to the π-system of a translationally related C8—C13 ring; C12'=O4···Cg(C18—C13) = 3.2061 (13)ii Å for ii: x, -1 + y, z. The double-chains stack in columns parallel to the b axis. Connections between columns are afforded by weak C—H···O contacts, involving an aromatic C4—H and O2 atoms, and weak C—H···N contacts involving aromatic C9—H and azo-N2 atoms, the latter leading to a eight-membered [···HCCN]2 synthon.

Related literature top

For related literature, see: Basu Baul et al. (1996, 2006, 2004).

Experimental top

2-[(E)-2-(3-Formyl-4-hydroxyphenyl)-1-diazenyl]benzoic acid (2.0 g, 7.40 mmol), prepared as in the literature (Basu Baul et al., 1996), was dissolved in anhydrous methanol (150 ml) and transferred to a three-necked round bottom flask equipped with a dropping funnel, water-cooled condenser and a guard tube, all placed in an ice/salt bath. The clear solution was allowed to cool as the stirring was continued. After sufficient cooling, SOCl2 (1.62 ml, 22.19 mmol) was added drop-wise over 30 min. The whole reaction mixture was allowed to warm to room temperature, stirred for 20 h, and then the volatiles were removed using a rotary evaporator. Water was added to the residue and neutralized with aqueous NaHCO3 solution. The product was extracted in ethyl acetate and the resulting two-phase system was mixed well and filtered, and the layers were separated. The ethyl acetate portion was washed with water, dried over Na2SO4, and the solvent was evaporated to one-fourth of its initial solvent volume and kept at room temperature to yield (I). The solid was washed with hexane, dried in vacuo and recrystallized from an ethyl acetate-methanol mixture (v/v, 1:1) which afforded the orange crystals (m.p. 333–335 K) in 85% (1.78 g) yield. Elemental analysis, found: C 63.41, H 4.27, N 9.87%; C15H12N2O4 requires C 63.37, H 4.25, N 9.85%. IR (KBr, cm-1): 1725 ν(OCO)asym. 1H NMR (CDCl3, 400.13 MHz): δ H: 11.37 [s, 1H, H4], 10.02 [s, 1H, H7], 8.41 [d, 2.6 Hz, 1H, H2], 8.19 [dd, 2.6, 8.8 Hz, 1H, H6], 7.83 [dd, 1.5, 7.7 Hz, 1H, H3'], 7.60 [dt, 1.5, 7.7 Hz, 2H, H4' & H6'], 7.51 [dt, 1.5, 7.7 Hz, 1H, H5'], 7.11 [d, 8.8 Hz, 1H, H5], 4.00 [s, 3H, H8'] p.p.m. 13C NMR (CDCl3, 100.62 MHz): δ C: 196.9, 168.2, 164.6, 152.1, 146.4, 132.5, 131.1, 130.4, 130.3, 130.2, 129.0, 120.7, 119.2, 119.0, 52.8 p.p.m.

Refinement top

All C-bound H atoms were included in the riding-model approximation, with C—H = 0.95 to 0.98 Å, and with Uiso(H) = 1.2Ueq(C). The hydroxyl-H atom was located from a difference map and included so that O—H = 0.84 Å and Uiso(H) = 1.5Ueq(O).

Structure description top

The synthesis of the title compound (I) and their interactions with triorganotin(IV) moieties, have attracted much interest owing to their novel structural possibilities (Basu Baul et al., 1996, 2006), and their significant biological activity towards mosquito larvae (Basu Baul et al., 2004) and sea urchin early development stages (Basu Baul et al., 2006).

Compound (I), Fig. 1, assumes an E-conformation. There is a twist in the molecule as seen in the N1—N2—C8—C9 and, in particular, the N2—N1—C7—C2 torsion angles of -163.77 (13) and -141.01 (14)°, respectively. This is also reflected in the dihedral angle of 59.77 (7)° formed between the C2—C7 and C8—C13 aromatic rings.

The hydroxyl group participates in an intramolecular O3—H···O4 hydrogen-bond and at the same time forms an intermolecular O3—H···O3 interaction with a centrosymmetric mate, Table 1, to form a double chain, Fig. 2. Additional stabilization to the chain are afforded by C—H···O1 contacts. Further, this arrangement allows for the close approach of the C=O4 carbonyl to the π-system of a translationally related C8—C13 ring; C12'=O4···Cg(C18—C13) = 3.2061 (13)ii Å for ii: x, -1 + y, z. The double-chains stack in columns parallel to the b axis. Connections between columns are afforded by weak C—H···O contacts, involving an aromatic C4—H and O2 atoms, and weak C—H···N contacts involving aromatic C9—H and azo-N2 atoms, the latter leading to a eight-membered [···HCCN]2 synthon.

For related literature, see: Basu Baul et al. (1996, 2006, 2004).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. View of the supramolecular chain in (I) mediated by hydrogen bonds, shown as orange-dashed lines. Colour code: red (oxygen), blue (nitrogen), grey (carbon) and green (hydrogen).
Methyl 2-[(E)-(3-formyl-4-hydroxyphenyl)diazenyl]benzoate top
Crystal data top
C15H12N2O4F(000) = 592
Mr = 284.27Dx = 1.444 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybcCell parameters from 2012 reflections
a = 14.164 (2) Åθ = 2.9–30.2°
b = 4.6113 (8) ŵ = 0.11 mm1
c = 21.067 (3) ÅT = 153 K
β = 108.140 (4)°Block, orange
V = 1307.6 (4) Å30.30 × 0.15 × 0.12 mm
Z = 4
Data collection top
Rigaku AFC12K/SATURN724
diffractometer
2638 independent reflections
Radiation source: fine-focus sealed tube2510 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 26.5°, θmin = 2.9°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1714
Tmin = 0.878, Tmax = 1k = 54
11141 measured reflectionsl = 2126
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0717P)2 + 0.3817P]
where P = (Fo2 + 2Fc2)/3
2638 reflections(Δ/σ)max = 0.001
194 parametersΔρmax = 0.21 e Å3
1 restraintΔρmin = 0.22 e Å3
Crystal data top
C15H12N2O4V = 1307.6 (4) Å3
Mr = 284.27Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.164 (2) ŵ = 0.11 mm1
b = 4.6113 (8) ÅT = 153 K
c = 21.067 (3) Å0.30 × 0.15 × 0.12 mm
β = 108.140 (4)°
Data collection top
Rigaku AFC12K/SATURN724
diffractometer
2638 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
2510 reflections with I > 2σ(I)
Tmin = 0.878, Tmax = 1Rint = 0.021
11141 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0461 restraint
wR(F2) = 0.129H-atom parameters constrained
S = 1.08Δρmax = 0.21 e Å3
2638 reflectionsΔρmin = 0.22 e Å3
194 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
O10.60419 (8)0.6564 (3)0.46402 (5)0.0425 (3)
O20.48259 (8)0.7820 (3)0.37164 (5)0.0439 (3)
O30.99285 (8)0.2764 (2)0.70389 (5)0.0360 (3)
H3O0.95180.40180.70750.054*
O40.82006 (8)0.5682 (2)0.67043 (5)0.0387 (3)
N10.74996 (9)0.3207 (3)0.43726 (6)0.0328 (3)
N20.84243 (9)0.3272 (3)0.46527 (6)0.0304 (3)
C10.57480 (10)0.6905 (3)0.40427 (7)0.0331 (3)
C20.63371 (10)0.6449 (3)0.35758 (7)0.0313 (3)
C30.60542 (11)0.7840 (3)0.29581 (8)0.0365 (4)
H30.54720.90060.28340.044*
C40.66068 (12)0.7554 (4)0.25217 (8)0.0397 (4)
H40.64080.85330.21040.048*
C50.74493 (12)0.5833 (4)0.26977 (8)0.0389 (4)
H50.78230.55990.23970.047*
C60.77477 (11)0.4460 (3)0.33085 (7)0.0348 (3)
H60.83280.32860.34260.042*
C70.72068 (10)0.4773 (3)0.37562 (7)0.0309 (3)
C80.87549 (10)0.1598 (3)0.52484 (7)0.0286 (3)
C90.97161 (10)0.2172 (3)0.56704 (7)0.0312 (3)
H91.01160.35640.55410.037*
C101.00897 (10)0.0743 (3)0.62710 (7)0.0322 (3)
H101.07340.12020.65600.039*
C110.95250 (10)0.1370 (3)0.64554 (7)0.0295 (3)
C120.85650 (10)0.2015 (3)0.60252 (7)0.0286 (3)
C12'0.79609 (11)0.4270 (3)0.61856 (7)0.0333 (3)
H12'0.73360.46810.58660.040*
C130.81883 (10)0.0505 (3)0.54276 (7)0.0291 (3)
H130.75380.09190.51410.035*
C140.42299 (11)0.8673 (5)0.41328 (9)0.0473 (4)
H14A0.42720.71750.44700.071*
H14B0.35370.89070.38550.071*
H14C0.44781.05140.43540.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0320 (5)0.0608 (8)0.0328 (6)0.0020 (5)0.0070 (4)0.0048 (5)
O20.0301 (5)0.0631 (8)0.0353 (6)0.0097 (5)0.0054 (5)0.0033 (5)
O30.0390 (6)0.0332 (6)0.0303 (6)0.0002 (4)0.0027 (5)0.0029 (4)
O40.0432 (6)0.0379 (6)0.0359 (6)0.0005 (5)0.0135 (5)0.0037 (5)
N10.0312 (6)0.0318 (7)0.0333 (7)0.0014 (5)0.0068 (5)0.0025 (5)
N20.0303 (6)0.0298 (6)0.0293 (6)0.0018 (5)0.0067 (5)0.0002 (5)
C10.0272 (7)0.0355 (8)0.0318 (8)0.0023 (6)0.0021 (6)0.0010 (6)
C20.0284 (7)0.0314 (7)0.0304 (8)0.0028 (5)0.0038 (6)0.0005 (6)
C30.0334 (7)0.0377 (8)0.0327 (8)0.0015 (6)0.0022 (6)0.0010 (6)
C40.0430 (8)0.0440 (9)0.0281 (8)0.0021 (7)0.0053 (6)0.0038 (6)
C50.0410 (8)0.0434 (9)0.0328 (8)0.0030 (7)0.0120 (6)0.0028 (7)
C60.0323 (7)0.0360 (8)0.0342 (8)0.0009 (6)0.0076 (6)0.0016 (6)
C70.0301 (7)0.0295 (7)0.0300 (7)0.0032 (5)0.0051 (5)0.0002 (5)
C80.0301 (7)0.0271 (7)0.0279 (7)0.0036 (5)0.0081 (5)0.0009 (5)
C90.0303 (7)0.0285 (7)0.0348 (8)0.0002 (5)0.0099 (6)0.0008 (6)
C100.0281 (7)0.0306 (7)0.0336 (8)0.0009 (6)0.0035 (6)0.0025 (6)
C110.0322 (7)0.0266 (7)0.0274 (7)0.0047 (5)0.0062 (5)0.0026 (5)
C120.0299 (7)0.0263 (7)0.0294 (7)0.0010 (5)0.0088 (5)0.0034 (5)
C12'0.0333 (7)0.0331 (8)0.0331 (8)0.0007 (6)0.0096 (6)0.0001 (6)
C130.0277 (6)0.0289 (7)0.0289 (7)0.0025 (5)0.0063 (5)0.0032 (5)
C140.0317 (8)0.0643 (11)0.0468 (10)0.0069 (8)0.0136 (7)0.0050 (8)
Geometric parameters (Å, º) top
C1—O11.2066 (19)C5—H50.9500
C1—O21.3407 (17)C6—C71.396 (2)
C14—O21.448 (2)C6—H60.9500
O3—C111.3467 (17)C8—C131.384 (2)
O3—H3O0.8401C8—C91.400 (2)
O4—C12'1.2257 (18)C9—C101.378 (2)
N1—N21.2582 (17)C9—H90.9500
N1—C71.4298 (18)C10—C111.390 (2)
N2—C81.4230 (18)C10—H100.9500
C1—C21.490 (2)C11—C121.4112 (19)
C2—C31.393 (2)C12—C131.392 (2)
C2—C71.402 (2)C12—C12'1.452 (2)
C3—C41.387 (2)C12'—H12'0.9500
C3—H30.9500C13—H130.9500
C4—C51.384 (2)C14—H14A0.9800
C4—H40.9500C14—H14B0.9800
C5—C61.377 (2)C14—H14C0.9800
C1—O2—C14115.68 (12)C13—C8—N2124.14 (12)
C11—O3—H3O107.5C9—C8—N2116.44 (12)
N2—N1—C7112.28 (12)C10—C9—C8120.81 (13)
N1—N2—C8114.16 (12)C10—C9—H9119.6
O1—C1—O2122.71 (14)C8—C9—H9119.6
O1—C1—C2126.03 (13)C9—C10—C11120.12 (13)
O2—C1—C2111.25 (12)C9—C10—H10119.9
C3—C2—C7118.68 (14)C11—C10—H10119.9
C3—C2—C1119.63 (13)O3—C11—C10118.16 (12)
C7—C2—C1121.60 (13)O3—C11—C12122.41 (13)
C2—C3—C4121.18 (14)C10—C11—C12119.43 (13)
C2—C3—H3119.4C13—C12—C11119.79 (13)
C4—C3—H3119.4C13—C12—C12'118.77 (13)
C5—C4—C3119.64 (14)C11—C12—C12'121.42 (13)
C5—C4—H4120.2O4—C12'—C12124.63 (13)
C3—C4—H4120.2O4—C12'—H12'117.7
C4—C5—C6120.14 (15)C12—C12'—H12'117.7
C4—C5—H5119.9C8—C13—C12120.39 (12)
C6—C5—H5119.9C8—C13—H13119.8
C7—C6—C5120.69 (14)C12—C13—H13119.8
C7—C6—H6119.7O2—C14—H14A109.5
C5—C6—H6119.7O2—C14—H14B109.5
C6—C7—C2119.64 (13)H14A—C14—H14B109.5
C6—C7—N1119.76 (13)O2—C14—H14C109.5
C2—C7—N1120.42 (13)H14A—C14—H14C109.5
C13—C8—C9119.41 (13)H14B—C14—H14C109.5
C7—N1—N2—C8176.49 (11)N2—N1—C7—C2141.01 (14)
C14—O2—C1—O16.2 (2)N1—N2—C8—C1316.02 (19)
C14—O2—C1—C2172.67 (14)N1—N2—C8—C9163.77 (13)
O1—C1—C2—C3157.39 (16)C13—C8—C9—C102.3 (2)
O2—C1—C2—C321.44 (19)N2—C8—C9—C10177.52 (12)
O1—C1—C2—C719.0 (2)C8—C9—C10—C112.2 (2)
O2—C1—C2—C7162.17 (13)C9—C10—C11—O3178.37 (12)
C7—C2—C3—C41.0 (2)C9—C10—C11—C120.6 (2)
C1—C2—C3—C4177.50 (14)O3—C11—C12—C13179.87 (12)
C2—C3—C4—C50.7 (2)C10—C11—C12—C131.0 (2)
C3—C4—C5—C61.3 (2)O3—C11—C12—C12'1.0 (2)
C4—C5—C6—C70.2 (2)C10—C11—C12—C12'177.91 (13)
C5—C6—C7—C21.5 (2)C13—C12—C12'—O4177.73 (13)
C5—C6—C7—N1176.71 (13)C11—C12—C12'—O43.4 (2)
C3—C2—C7—C62.1 (2)C9—C8—C13—C120.7 (2)
C1—C2—C7—C6178.52 (13)N2—C8—C13—C12179.08 (12)
C3—C2—C7—N1177.23 (13)C11—C12—C13—C80.9 (2)
C1—C2—C7—N16.3 (2)C12'—C12—C13—C8178.02 (13)
N2—N1—C7—C643.86 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O40.841.942.6876 (16)147
O3—H3O···O3i0.842.482.9810 (15)119
C13—H13···O1ii0.952.363.268 (2)160
C9—H9···N2iii0.952.663.596 (2)167
C4—H4···O2iv0.952.843.677 (2)147
Symmetry codes: (i) x+2, y1/2, z+3/2; (ii) x, y1, z; (iii) x+2, y+1, z+1; (iv) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H12N2O4
Mr284.27
Crystal system, space groupMonoclinic, P21/c
Temperature (K)153
a, b, c (Å)14.164 (2), 4.6113 (8), 21.067 (3)
β (°) 108.140 (4)
V3)1307.6 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.30 × 0.15 × 0.12
Data collection
DiffractometerRigaku AFC12K/SATURN724
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.878, 1
No. of measured, independent and
observed [I > 2σ(I)] reflections
11141, 2638, 2510
Rint0.021
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.129, 1.08
No. of reflections2638
No. of parameters194
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.22

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalClear, SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O40.841.942.6876 (16)147
O3—H3O···O3i0.842.482.9810 (15)119
C13—H13···O1ii0.952.363.268 (2)160
C9—H9···N2iii0.952.663.596 (2)167
C4—H4···O2iv0.952.843.677 (2)147
Symmetry codes: (i) x+2, y1/2, z+3/2; (ii) x, y1, z; (iii) x+2, y+1, z+1; (iv) x+1, y+1/2, z+1/2.
 

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