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The title compound, C16H17NO5, crystallizes with two mol­ecules in the asymmetric unit. The dihedral angles between the furan and benzene rings are 26.38 (13) and 28.52 (14)°. The mol­ecules are linked by N—H...O hydrogen bonds, leading to dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805032307/hg6253sup1.cif
Contains datablocks global, 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805032307/hg62531sup2.hkl
Contains datablock 1

CCDC reference: 289767

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.053
  • wR factor = 0.159
  • Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.13 Ratio PLAT420_ALERT_2_C D-H Without Acceptor N2 - H201 ... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H201 .. O2 .. 2.64 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003).

Dimethyl 3-(methylamino)-2-(4-methylphenyl)furan-4,5-dicarboxylate top
Crystal data top
C16H17NO5F(000) = 1280.00
Mr = 303.31Dx = 1.319 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 12870 reflections
a = 15.5390 (2) Åθ = 1.8–27.5°
b = 17.8363 (3) ŵ = 0.10 mm1
c = 11.6349 (3) ÅT = 295 K
β = 108.6580 (7)°Prism, yellow
V = 3055.23 (10) Å30.30 × 0.20 × 0.10 mm
Z = 8
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3442 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.050
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 2020
Tmin = 0.943, Tmax = 0.990k = 2323
28950 measured reflectionsl = 1514
6994 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.053 w = 1/[0.0014Fo2 + 1σ(Fo2)]/(4Fo2)
wR(F2) = 0.159(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.57 e Å3
6992 reflectionsΔρmin = 0.59 e Å3
397 parameters
Special details top

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.19334 (11)0.55133 (9)0.60462 (14)0.0438 (5)
O20.13246 (12)0.30854 (10)0.47869 (17)0.0586 (6)
O30.12175 (12)0.33308 (9)0.66288 (14)0.0487 (5)
O40.00263 (12)0.46164 (11)0.64034 (18)0.0569 (6)
O50.07660 (12)0.56647 (10)0.72350 (17)0.0579 (6)
O60.32307 (11)0.51294 (9)0.92235 (16)0.0467 (5)
O70.29690 (12)0.25939 (10)0.90574 (17)0.0573 (6)
O80.33441 (12)0.30705 (10)0.75115 (16)0.0511 (5)
O90.48171 (12)0.41124 (11)0.8276 (2)0.0645 (6)
O100.44858 (12)0.53331 (10)0.82024 (18)0.0605 (6)
N10.28585 (13)0.40982 (12)0.45587 (19)0.0467 (6)
N20.17956 (12)0.36918 (12)0.97855 (19)0.0436 (6)
C10.25200 (17)0.52907 (13)0.5430 (2)0.0422 (7)
C20.24027 (16)0.45424 (12)0.5171 (2)0.0390 (7)
C30.17029 (16)0.42928 (12)0.5638 (2)0.0380 (6)
C40.14308 (16)0.49067 (13)0.6136 (2)0.0409 (7)
C50.30801 (17)0.58925 (12)0.5188 (2)0.0408 (7)
C60.32681 (19)0.65345 (14)0.5906 (2)0.0514 (8)
C70.37400 (18)0.71244 (14)0.5623 (2)0.0538 (8)
C80.40382 (17)0.71026 (14)0.4619 (2)0.0493 (8)
C90.4521 (2)0.77634 (17)0.4303 (3)0.0743 (11)
C100.38659 (18)0.64553 (17)0.3920 (2)0.0538 (8)
C110.33968 (17)0.58587 (14)0.4190 (2)0.0468 (7)
C120.13875 (16)0.35145 (13)0.5616 (2)0.0412 (7)
C130.0852 (2)0.25869 (14)0.6658 (2)0.0632 (10)
C140.06647 (19)0.50340 (13)0.6596 (2)0.0433 (7)
C150.0045 (2)0.58471 (18)0.7720 (2)0.0681 (10)
C160.38497 (18)0.40661 (16)0.5051 (2)0.0575 (9)
C170.25543 (16)0.48947 (13)0.9677 (2)0.0422 (7)
C180.24219 (16)0.41455 (13)0.9491 (2)0.0390 (7)
C190.30580 (16)0.39020 (12)0.8905 (2)0.0380 (6)
C200.35412 (16)0.45188 (13)0.8787 (2)0.0404 (7)
C210.21895 (17)0.54724 (14)1.0280 (2)0.0458 (7)
C220.2190 (2)0.62213 (16)0.9966 (2)0.0616 (9)
C230.1877 (2)0.67608 (18)1.0574 (3)0.0771 (11)
C240.1560 (2)0.6579 (2)1.1527 (3)0.0749 (11)
C250.1273 (2)0.7183 (2)1.2243 (4)0.1187 (17)
C260.15381 (19)0.5835 (2)1.1813 (2)0.0670 (10)
C270.18474 (18)0.52863 (17)1.1206 (2)0.0547 (8)
C280.31275 (16)0.31266 (13)0.8525 (2)0.0392 (7)
C290.3510 (2)0.23199 (16)0.7162 (2)0.0672 (10)
C300.43449 (18)0.46157 (14)0.8395 (2)0.0433 (7)
C310.5268 (2)0.54973 (19)0.7831 (3)0.0737 (11)
C320.08478 (17)0.39031 (16)0.9368 (2)0.0526 (8)
H60.30730.65680.65810.064*
H70.38630.75470.61180.065*
H100.40660.64240.32490.066*
H110.32980.54290.37130.056*
H220.24010.63610.93330.077*
H230.18820.72601.03470.094*
H260.13110.56981.24330.081*
H270.18280.47861.14220.065*
H910.40850.80930.37690.090*
H920.49400.75890.39080.090*
H930.48480.80290.50300.090*
H1010.26110.36610.44240.059*
H1310.02010.26040.63460.083*
H1320.10390.24080.74790.083*
H1330.10750.22550.61690.083*
H1510.04000.61480.71420.088*
H1520.02880.61220.84640.088*
H1530.02340.53940.78730.088*
H1610.41080.44550.46940.073*
H1620.40550.35870.48680.073*
H1630.40360.41340.59140.074*
H2010.19700.32941.02140.055*
H2510.17880.73331.29150.147*
H2520.08080.69901.25400.147*
H2530.10430.76081.17300.147*
H2910.41420.22010.75210.086*
H2920.33480.22920.62950.086*
H2930.31510.19690.74390.086*
H3110.57920.55830.85290.095*
H3120.51470.59370.73290.095*
H3130.53810.50800.73780.095*
H3210.04790.34600.92510.066*
H3220.07170.41690.86140.066*
H3230.07180.42200.99600.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0489 (10)0.0333 (9)0.0549 (11)0.0010 (8)0.0247 (9)0.0013 (8)
O20.0809 (14)0.0455 (11)0.0589 (12)0.0111 (10)0.0357 (11)0.0128 (9)
O30.0648 (11)0.0376 (10)0.0498 (10)0.0075 (8)0.0271 (10)0.0016 (8)
O40.0491 (11)0.0573 (12)0.0698 (13)0.0022 (10)0.0268 (10)0.0008 (10)
O50.0655 (12)0.0467 (11)0.0734 (13)0.0047 (9)0.0391 (11)0.0101 (9)
O60.0480 (10)0.0392 (10)0.0584 (11)0.0053 (8)0.0245 (9)0.0060 (8)
O70.0815 (14)0.0376 (10)0.0661 (13)0.0057 (9)0.0421 (11)0.0098 (9)
O80.0686 (12)0.0441 (10)0.0496 (11)0.0034 (9)0.0316 (10)0.0016 (8)
O90.0594 (12)0.0562 (12)0.0913 (15)0.0065 (10)0.0429 (12)0.0021 (11)
O100.0605 (12)0.0455 (11)0.0899 (15)0.0079 (9)0.0441 (12)0.0021 (10)
N10.0507 (13)0.0400 (12)0.0562 (13)0.0023 (10)0.0264 (11)0.0090 (10)
N20.0425 (12)0.0425 (12)0.0503 (12)0.0021 (10)0.0210 (11)0.0127 (10)
C10.0448 (14)0.0386 (14)0.0472 (15)0.0020 (11)0.0206 (13)0.0000 (11)
C20.0418 (13)0.0356 (14)0.0414 (14)0.0014 (11)0.0159 (12)0.0003 (11)
C30.0416 (13)0.0345 (13)0.0390 (14)0.0018 (11)0.0143 (12)0.0017 (11)
C40.0423 (14)0.0362 (14)0.0466 (14)0.0002 (11)0.0176 (12)0.0038 (11)
C50.0411 (14)0.0343 (13)0.0477 (15)0.0039 (11)0.0155 (12)0.0028 (11)
C60.0594 (17)0.0444 (16)0.0557 (17)0.0018 (13)0.0258 (14)0.0044 (13)
C70.0588 (17)0.0376 (15)0.0661 (19)0.0047 (13)0.0214 (16)0.0012 (13)
C80.0400 (14)0.0438 (16)0.0613 (18)0.0004 (12)0.0124 (14)0.0090 (13)
C90.072 (2)0.064 (2)0.087 (2)0.0183 (17)0.026 (2)0.0118 (18)
C100.0526 (16)0.0601 (18)0.0526 (17)0.0016 (14)0.0222 (14)0.0067 (14)
C110.0505 (15)0.0423 (15)0.0486 (16)0.0049 (12)0.0172 (13)0.0005 (12)
C120.0402 (14)0.0381 (14)0.0469 (15)0.0040 (11)0.0162 (12)0.0007 (12)
C130.086 (2)0.0407 (16)0.079 (2)0.0155 (15)0.0489 (19)0.0015 (14)
C140.0499 (15)0.0385 (14)0.0448 (14)0.0102 (13)0.0199 (13)0.0075 (12)
C150.076 (2)0.065 (2)0.079 (2)0.0221 (17)0.0459 (19)0.0007 (16)
C160.0568 (17)0.0525 (17)0.072 (2)0.0052 (14)0.0338 (16)0.0046 (14)
C170.0389 (13)0.0456 (15)0.0465 (15)0.0020 (11)0.0196 (12)0.0010 (12)
C180.0403 (13)0.0399 (14)0.0383 (14)0.0015 (11)0.0145 (12)0.0015 (11)
C190.0397 (14)0.0385 (14)0.0380 (13)0.0010 (11)0.0158 (11)0.0011 (11)
C200.0441 (14)0.0357 (14)0.0432 (14)0.0018 (11)0.0164 (12)0.0018 (11)
C210.0404 (14)0.0451 (16)0.0523 (16)0.0031 (12)0.0156 (13)0.0128 (12)
C220.0603 (18)0.0493 (18)0.083 (2)0.0054 (14)0.0335 (17)0.0135 (15)
C230.064 (2)0.0458 (19)0.126 (3)0.0053 (15)0.037 (2)0.0276 (19)
C240.0446 (17)0.082 (2)0.098 (2)0.0086 (17)0.0240 (18)0.049 (2)
C250.086 (2)0.114 (3)0.166 (4)0.014 (2)0.055 (3)0.090 (3)
C260.0468 (17)0.093 (2)0.064 (2)0.0045 (17)0.0222 (15)0.0266 (18)
C270.0476 (15)0.0644 (19)0.0523 (16)0.0006 (14)0.0163 (14)0.0114 (14)
C280.0386 (13)0.0412 (15)0.0393 (14)0.0027 (11)0.0147 (12)0.0020 (11)
C290.089 (2)0.0556 (19)0.070 (2)0.0118 (17)0.0428 (19)0.0110 (15)
C300.0446 (15)0.0434 (15)0.0440 (15)0.0046 (13)0.0170 (13)0.0006 (12)
C310.066 (2)0.068 (2)0.102 (2)0.0185 (17)0.048 (2)0.0042 (18)
C320.0459 (16)0.0559 (17)0.0611 (18)0.0033 (13)0.0242 (14)0.0049 (14)
Geometric parameters (Å, º) top
O1—C11.386 (3)C21—C271.385 (4)
O1—C41.358 (3)C22—C231.373 (5)
O2—C121.211 (3)C23—C241.388 (5)
O3—C121.328 (3)C24—C251.513 (6)
O3—C131.448 (3)C24—C261.371 (5)
O4—C141.203 (3)C26—C271.381 (4)
O5—C141.329 (3)N1—H1010.862
O5—C151.444 (4)N2—H2010.860
O6—C171.383 (3)C6—H60.930
O6—C201.354 (3)C7—H70.930
O7—C281.202 (3)C9—H910.960
O8—C281.329 (3)C9—H920.960
O8—C291.446 (3)C9—H930.960
O9—C301.195 (3)C10—H100.930
O10—C301.329 (3)C11—H110.930
O10—C311.445 (4)C13—H1310.960
N1—C21.400 (3)C13—H1320.960
N1—C161.463 (3)C13—H1330.960
N2—C181.390 (3)C15—H1510.960
N2—C321.445 (3)C15—H1520.960
C1—C21.368 (3)C15—H1530.960
C1—C51.465 (3)C16—H1610.960
C2—C31.434 (3)C16—H1620.960
C3—C41.368 (3)C16—H1630.960
C3—C121.470 (3)C22—H220.930
C4—C141.471 (4)C23—H230.930
C5—C61.392 (3)C25—H2510.960
C5—C111.400 (4)C25—H2520.960
C6—C71.381 (4)C25—H2530.960
C7—C81.389 (4)C26—H260.930
C8—C91.505 (4)C27—H270.930
C8—C101.388 (4)C29—H2910.960
C10—C111.381 (4)C29—H2920.960
C17—C181.359 (3)C29—H2930.960
C17—C211.460 (3)C31—H3110.960
C18—C191.436 (3)C31—H3120.960
C19—C201.363 (3)C31—H3130.960
C19—C281.467 (3)C32—H3210.960
C20—C301.471 (4)C32—H3220.960
C21—C221.385 (3)C32—H3230.960
C1—O1—C4107.54 (19)C18—N2—H201120.5
C12—O3—C13115.9 (2)C32—N2—H201120.6
C14—O5—C15116.2 (2)C5—C6—H6119.7
C17—O6—C20107.76 (19)C7—C6—H6119.6
C28—O8—C29115.9 (2)C6—C7—H7119.2
C30—O10—C31116.4 (2)C8—C7—H7119.1
C2—N1—C16117.6 (2)C8—C9—H91109.5
C18—N2—C32118.9 (2)C8—C9—H92109.3
O1—C1—C2109.3 (2)C8—C9—H93109.6
O1—C1—C5114.8 (2)H91—C9—H92109.5
C2—C1—C5135.9 (2)H91—C9—H93109.5
N1—C2—C1127.7 (2)H92—C9—H93109.5
N1—C2—C3125.9 (2)C8—C10—H10119.2
C1—C2—C3106.4 (2)C11—C10—H10119.1
C2—C3—C4106.7 (2)C5—C11—H11119.7
C2—C3—C12125.2 (2)C10—C11—H11119.9
C4—C3—C12128.1 (2)O3—C13—H131109.7
O1—C4—C3110.0 (2)O3—C13—H132109.3
O1—C4—C14117.2 (2)O3—C13—H133109.4
C3—C4—C14132.4 (2)H131—C13—H132109.5
C1—C5—C6120.8 (2)H131—C13—H133109.5
C1—C5—C11121.0 (2)H132—C13—H133109.5
C6—C5—C11118.1 (2)O5—C15—H151109.2
C5—C6—C7120.6 (2)O5—C15—H152109.7
C6—C7—C8121.7 (2)O5—C15—H153109.6
C7—C8—C9120.7 (2)H151—C15—H152109.5
C7—C8—C10117.5 (2)H151—C15—H153109.5
C9—C8—C10121.8 (3)H152—C15—H153109.5
C8—C10—C11121.7 (2)N1—C16—H161109.7
C5—C11—C10120.4 (2)N1—C16—H162109.3
O2—C12—O3124.2 (2)N1—C16—H163109.4
O2—C12—C3123.5 (2)H161—C16—H162109.5
O3—C12—C3112.2 (2)H161—C16—H163109.5
O4—C14—O5124.9 (2)H162—C16—H163109.5
O4—C14—C4123.5 (2)C21—C22—H22119.8
O5—C14—C4111.7 (2)C23—C22—H22119.6
O6—C17—C18109.4 (2)C22—C23—H23119.3
O6—C17—C21115.4 (2)C24—C23—H23119.1
C18—C17—C21135.1 (2)C24—C25—H251109.4
N2—C18—C17128.0 (2)C24—C25—H252109.3
N2—C18—C19125.7 (2)C24—C25—H253109.7
C17—C18—C19106.3 (2)H251—C25—H252109.5
C18—C19—C20106.8 (2)H251—C25—H253109.5
C18—C19—C28123.8 (2)H252—C25—H253109.5
C20—C19—C28129.4 (2)C24—C26—H26119.2
O6—C20—C19109.7 (2)C27—C26—H26119.3
O6—C20—C30117.5 (2)C21—C27—H27119.6
C19—C20—C30132.5 (2)C26—C27—H27119.7
C17—C21—C22121.3 (2)O8—C29—H291109.4
C17—C21—C27120.6 (2)O8—C29—H292109.5
C22—C21—C27118.0 (2)O8—C29—H293109.6
C21—C22—C23120.6 (3)H291—C29—H292109.5
C22—C23—C24121.6 (3)H291—C29—H293109.5
C23—C24—C25121.1 (3)H292—C29—H293109.5
C23—C24—C26117.6 (3)O10—C31—H311110.2
C25—C24—C26121.3 (3)O10—C31—H312109.1
C24—C26—C27121.5 (3)O10—C31—H313109.0
C21—C27—C26120.7 (2)H311—C31—H312109.5
O7—C28—O8123.3 (2)H311—C31—H313109.5
O7—C28—C19122.9 (2)H312—C31—H313109.5
O8—C28—C19113.7 (2)N2—C32—H321109.4
O9—C30—O10124.3 (2)N2—C32—H322109.3
O9—C30—C20124.1 (2)N2—C32—H323109.8
O10—C30—C20111.6 (2)H321—C32—H322109.5
C2—N1—H101109.6H321—C32—H323109.5
C16—N1—H101112.9H322—C32—H323109.5
C1—O1—C4—C32.4 (2)C1—C5—C6—C7175.2 (2)
C1—O1—C4—C14171.06 (18)C1—C5—C11—C10175.1 (2)
C4—O1—C1—C21.9 (2)C6—C5—C11—C101.3 (3)
C4—O1—C1—C5176.56 (18)C11—C5—C6—C71.1 (3)
C13—O3—C12—O26.1 (3)C5—C6—C7—C80.4 (3)
C13—O3—C12—C3176.5 (2)C6—C7—C8—C9177.8 (2)
C15—O5—C14—O40.0 (2)C6—C7—C8—C101.7 (3)
C15—O5—C14—C4179.4 (2)C7—C8—C10—C111.5 (3)
C17—O6—C20—C192.3 (2)C9—C8—C10—C11177.9 (2)
C17—O6—C20—C30172.52 (18)C8—C10—C11—C50.1 (2)
C20—O6—C17—C181.9 (2)O6—C17—C18—N2178.60 (19)
C20—O6—C17—C21175.10 (18)O6—C17—C18—C190.7 (2)
C29—O8—C28—O78.6 (3)O6—C17—C21—C2228.0 (3)
C29—O8—C28—C19174.1 (2)O6—C17—C21—C27150.7 (2)
C31—O10—C30—O90.2 (3)C18—C17—C21—C22156.0 (2)
C31—O10—C30—C20179.0 (2)C18—C17—C21—C2725.3 (3)
C16—N1—C2—C157.1 (3)C21—C17—C18—N25.2 (4)
C16—N1—C2—C3123.8 (2)C21—C17—C18—C19175.4 (2)
C32—N2—C18—C1753.0 (3)N2—C18—C19—C20180.0 (2)
C32—N2—C18—C19126.2 (2)N2—C18—C19—C280.4 (3)
O1—C1—C2—N1179.92 (19)C17—C18—C19—C200.7 (2)
O1—C1—C2—C30.6 (2)C17—C18—C19—C28178.90 (19)
O1—C1—C5—C623.9 (3)C18—C19—C20—O61.9 (2)
O1—C1—C5—C11152.4 (2)C18—C19—C20—C30171.9 (2)
C2—C1—C5—C6158.3 (2)C18—C19—C28—O731.7 (3)
C2—C1—C5—C1125.5 (3)C18—C19—C28—O8145.7 (2)
C5—C1—C2—N11.9 (4)C20—C19—C28—O7148.8 (2)
C5—C1—C2—C3177.3 (2)C20—C19—C28—O833.8 (3)
N1—C2—C3—C4178.5 (2)C28—C19—C20—O6177.7 (2)
N1—C2—C3—C124.0 (3)C28—C19—C20—C308.5 (4)
C1—C2—C3—C40.8 (2)O6—C20—C30—O9160.9 (2)
C1—C2—C3—C12176.7 (2)O6—C20—C30—O1018.3 (2)
C2—C3—C4—O12.0 (2)C19—C20—C30—O912.5 (4)
C2—C3—C4—C14170.1 (2)C19—C20—C30—O10168.2 (2)
C2—C3—C12—O236.7 (3)C17—C21—C22—C23177.5 (2)
C2—C3—C12—O3140.7 (2)C17—C21—C27—C26177.2 (2)
C4—C3—C12—O2146.3 (2)C22—C21—C27—C261.6 (3)
C4—C3—C12—O336.3 (3)C27—C21—C22—C231.3 (3)
C12—C3—C4—O1175.43 (19)C21—C22—C23—C240.7 (4)
C12—C3—C4—C1412.4 (4)C22—C23—C24—C25176.0 (2)
O1—C4—C14—O4157.8 (2)C22—C23—C24—C262.4 (4)
O1—C4—C14—O521.6 (2)C23—C24—C26—C272.1 (4)
C3—C4—C14—O413.9 (4)C25—C24—C26—C27176.3 (2)
C3—C4—C14—O5166.7 (2)C24—C26—C27—C210.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H101···O7i0.862.383.089 (3)140
N2—H201···O2ii0.862.643.253 (2)129
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y+1/2, z+1/2.
 

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