Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 5| May 2009| Page o1101
doi:10.1107/S1600536809014627

N-Phenyl­maleamic acid

Kong Mun Loa and Seik Weng Nga*

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 18 April 2009; accepted 20 April 2009; online 25 April 2009)

The two independent mol­ecules in the title compound (systematic name: 4-amino-4-oxobut-2-enoic acid), C10H9NO3, are both essentially planar (r.m.s. deviations = 0.05 and 0.06 Å). In both mol­ecules, the –OH group forms an intra­molecular hydrogen bond to the amide O atom. Adjacent mol­ecules are linked by N—H⋯O hydrogen bonds into a flat ribbon that runs along the a axis of the monoclinic unit cell.

Related literature

For the crystal structures of other substituted N-(phen­yl)maleamic acids, see, for example: Gonzalez-Rodriguez et al. (1986[Gonzalez-Rodriguez, J., Canoira, L., Calderon, C. E., Martinez-Ripoll, M. & García Blanco, S. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 199-203.]); Home et al. (1991[Home, S., Taylor, N., Colins, S. & Rodrigo, R. (1991). J. Chem. Soc. Perkin Trans. 1, pp. 3047-3051.]); Lynch & McClenaghan (2002[Lynch, D. E. & McClenaghan, I. (2002). Acta Cryst. E58, o678-o679.]); Parvez et al. (2004a[Parvez, M., Shahid, K., Shahzadi, S. & Ali, S. (2004a). Acta Cryst. E60, o2079-o2081.],b[Parvez, M., Shahzadi, S., Shahid, K. & Ali, S. (2004b). Acta Cryst. E60, o2082-o2084.]); Prasad et al. (2002a[Prasad, S. M., Sinha, R. B. P., Mandal, D. K. & Rani, A. (2002a). Acta Cryst. E58, o1296-o1297.],b[Prasad, S. M., Sinha, R. B. P., Mandal, D. K. & Rani, A. (2002b). Acta Cryst. E58, o891-o892.]); Santos-Sánchez et al. (2007[Santos-Sánchez, N. F., Salas-Coronado, R., Peña-Hueso, A. & Flores-Parra, A. (2007). Acta Cryst. E63, o4156.]); Wardell et al. (2005[Wardell, J. L., Skakle, J. M. S., Low, J. N. & Glidewell, C. (2005). Acta Cryst. E61, o3849-o3851.]).

[Scheme 1]

Experimental

Crystal data

  • C10H9NO3

  • Mr = 191.18

  • Monoclinic, P 21 /c

  • a = 12.7505 (4) Å

  • b = 10.5849 (5) Å

  • c = 14.1918 (6) Å

  • β = 116.299 (3)°

  • V = 1717.1 (1) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 100 K

  • 0.24 × 0.06 × 0.06 mm
Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 11493 measured reflections

  • 3925 independent reflections

  • 2256 reflections with I > 2σ(I)

  • Rint = 0.062
Refinement

  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.208

  • S = 1.02

  • 3925 reflections

  • 269 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.96 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2o⋯O3 0.85 (1) 1.63 (1) 2.475 (3) 172 (4)
O5—H5o⋯O6 0.86 (1) 1.65 (1) 2.496 (3) 170 (3)
N1—H1n⋯O4 0.88 (1) 2.00 (1) 2.864 (3) 166 (3)
N2—H2n⋯O1i 0.89 (1) 1.99 (1) 2.859 (3) 167 (3)
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014627/tk2436sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014627/tk2436Isup2.hkl

checkCIF report


Related literature top

For the crystal structures of other substituted N-(phenyl)maleamic acids, see, for example: Gonzalez-Rodriguez et al. (1986); Home et al. (1991); Lynch & McClenaghan (2002); Parvez et al. (2004a,b); Prasad et al. (2002a,b); Santos-Sánchez et al. (2007); Wardell et al. (2005).

Experimental top

Maleic anhydride (1 g, 1 mmol) and aniline (1 ml, 1 mmol) was heated in toluene (50 ml) for 1 h. The solution was set aside for the formation of crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The oxygen- and nitrogen-bound hydrogen atoms were located in a difference Fourier map, and were refined with distance restraints of O–H 0.84±0.01 Å and N–H 0.88±0.01 Å; the temperature factors were refined.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C10H9NO3 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
4-amino-4-oxobut-2-enoic acid top
Crystal data top
C10H9NO3F(000) = 800
Mr = 191.18Dx = 1.479 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1202 reflections
a = 12.7505 (4) Åθ = 2.6–27.4°
b = 10.5849 (5) ŵ = 0.11 mm−1
c = 14.1918 (6) ÅT = 100 K
β = 116.299 (3)°Prism, colorless
V = 1717.1 (1) Å30.24 × 0.06 × 0.06 mm
Z = 8
Data collection top
Bruker SMART APEX
diffractometer		2256 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.062
Graphite monochromatorθmax = 27.5°, θmin = 1.8°
ω scansh = −16→16
11493 measured reflectionsk = −13→13
3925 independent reflectionsl = −14→18
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.1139P)2]
where P = (Fo2 + 2Fc2)/3
3925 reflections(Δ/σ)max = 0.001
269 parametersΔρmax = 0.96 e Å−3
4 restraintsΔρmin = −0.36 e Å−3
Crystal data top
C10H9NO3V = 1717.1 (1) Å3
Mr = 191.18Z = 8
Monoclinic, P21/cMo Kα radiation
a = 12.7505 (4) ŵ = 0.11 mm−1
b = 10.5849 (5) ÅT = 100 K
c = 14.1918 (6) Å0.24 × 0.06 × 0.06 mm
β = 116.299 (3)°
Data collection top
Bruker SMART APEX
diffractometer		2256 reflections with I > 2σ(I)
11493 measured reflectionsRint = 0.062
3925 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0684 restraints
wR(F2) = 0.208H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.96 e Å−3
3925 reflectionsΔρmin = −0.36 e Å−3
269 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.41604 (16)0.86211 (19)0.61750 (16)0.0173 (5)
O20.41080 (17)0.6545 (2)0.62972 (17)0.0167 (5)
H2O0.449 (3)0.590 (3)0.627 (3)0.058 (14)*
O30.53761 (17)0.4779 (2)0.62899 (16)0.0187 (5)
O40.91395 (17)0.5468 (2)0.60999 (17)0.0216 (5)
O50.91031 (17)0.75293 (19)0.62870 (17)0.0164 (5)
H5O0.946 (3)0.820 (2)0.625 (3)0.028 (10)*
O61.03470 (16)0.93320 (19)0.62520 (16)0.0187 (5)
N10.7136 (2)0.4490 (2)0.62704 (18)0.0122 (5)
H1N0.771 (2)0.492 (3)0.623 (2)0.019 (8)*
N21.2093 (2)0.9624 (2)0.62037 (19)0.0149 (6)
H2N1.2657 (19)0.923 (3)0.611 (2)0.020 (8)*
C10.4591 (2)0.7584 (3)0.6178 (2)0.0123 (6)
C20.5691 (2)0.7538 (3)0.6046 (2)0.0109 (6)
H20.59330.83360.59060.013*
C30.6396 (2)0.6584 (3)0.6087 (2)0.0157 (6)
H30.70790.68110.60180.019*
C40.6250 (2)0.5224 (3)0.6227 (2)0.0135 (6)
C50.7229 (2)0.3155 (3)0.6348 (2)0.0130 (6)
C60.8169 (2)0.2612 (3)0.6232 (2)0.0118 (6)
H60.87100.31390.61250.014*
C70.8311 (2)0.1321 (3)0.6272 (2)0.0164 (6)
H70.89450.09570.61880.020*
C80.7521 (2)0.0547 (3)0.6436 (2)0.0149 (6)
H80.7609−0.03450.64500.018*
C90.6615 (2)0.1075 (3)0.6576 (2)0.0171 (6)
H90.60860.05440.66970.020*
C100.6463 (2)0.2388 (3)0.6541 (2)0.0136 (6)
H100.58430.27490.66480.016*
C110.9577 (2)0.6509 (3)0.6128 (2)0.0145 (6)
C121.0671 (2)0.6566 (3)0.5988 (2)0.0171 (6)
H121.09100.57730.58360.021*
C131.1380 (2)0.7531 (3)0.6038 (2)0.0095 (6)
H131.20700.73130.59770.011*
C141.1215 (2)0.8896 (3)0.6177 (2)0.0140 (6)
C151.2203 (2)1.0966 (3)0.6289 (2)0.0130 (6)
C161.3130 (2)1.1490 (3)0.6154 (2)0.0169 (7)
H161.36451.09610.60120.020*
C171.3298 (2)1.2781 (3)0.6228 (2)0.0163 (6)
H171.39341.31360.61430.020*
C181.2542 (2)1.3569 (3)0.6427 (2)0.0165 (6)
H181.26591.44580.64710.020*
C191.1619 (2)1.3044 (3)0.6560 (2)0.0147 (6)
H191.10971.35760.66890.018*
C201.1457 (2)1.1746 (3)0.6504 (2)0.0147 (6)
H201.08351.13880.66120.018*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0154 (10)0.0149 (12)0.0241 (12)0.0036 (8)0.0111 (9)−0.0025 (9)
O20.0143 (10)0.0118 (12)0.0283 (12)0.0004 (9)0.0133 (9)0.0026 (9)
O30.0165 (10)0.0144 (12)0.0298 (12)−0.0003 (8)0.0145 (9)0.0015 (9)
O40.0195 (10)0.0149 (12)0.0335 (13)−0.0042 (9)0.0145 (10)−0.0003 (9)
O50.0150 (10)0.0108 (12)0.0280 (13)−0.0026 (8)0.0138 (9)0.0000 (9)
O60.0176 (10)0.0126 (12)0.0322 (13)−0.0003 (9)0.0166 (9)−0.0029 (9)
N10.0159 (12)0.0072 (13)0.0159 (12)−0.0001 (10)0.0091 (10)0.0012 (10)
N20.0145 (12)0.0157 (14)0.0175 (13)0.0013 (10)0.0097 (10)0.0010 (10)
C10.0106 (13)0.0144 (16)0.0125 (15)0.0004 (11)0.0057 (11)−0.0015 (11)
C20.0111 (13)0.0083 (15)0.0136 (14)−0.0008 (10)0.0057 (11)−0.0022 (11)
C30.0166 (13)0.0157 (17)0.0185 (15)−0.0007 (12)0.0112 (12)−0.0009 (12)
C40.0135 (13)0.0150 (16)0.0128 (14)0.0017 (11)0.0067 (11)−0.0012 (11)
C50.0149 (13)0.0136 (15)0.0106 (14)0.0022 (12)0.0056 (11)0.0007 (12)
C60.0127 (13)0.0119 (15)0.0128 (14)−0.0023 (11)0.0075 (11)0.0004 (11)
C70.0161 (13)0.0162 (17)0.0165 (15)0.0017 (12)0.0068 (12)−0.0009 (12)
C80.0231 (14)0.0050 (14)0.0177 (15)−0.0012 (11)0.0101 (12)−0.0002 (11)
C90.0166 (13)0.0175 (17)0.0171 (15)−0.0020 (12)0.0075 (12)0.0044 (12)
C100.0094 (12)0.0195 (17)0.0122 (15)0.0029 (11)0.0049 (11)0.0005 (12)
C110.0151 (13)0.0139 (16)0.0159 (15)0.0000 (12)0.0082 (12)0.0018 (12)
C120.0197 (14)0.0182 (17)0.0175 (15)0.0032 (12)0.0119 (12)0.0005 (12)
C130.0114 (12)0.0100 (14)0.0075 (13)0.0000 (10)0.0044 (10)−0.0009 (10)
C140.0176 (13)0.0158 (16)0.0091 (14)0.0013 (12)0.0064 (11)0.0009 (11)
C150.0176 (13)0.0107 (15)0.0084 (13)0.0042 (11)0.0037 (11)0.0025 (11)
C160.0171 (14)0.0180 (17)0.0167 (15)0.0033 (12)0.0083 (12)0.0000 (12)
C170.0105 (13)0.0211 (17)0.0164 (15)−0.0028 (12)0.0051 (11)0.0027 (13)
C180.0173 (14)0.0139 (16)0.0154 (15)−0.0052 (12)0.0046 (12)−0.0002 (12)
C190.0135 (13)0.0141 (16)0.0155 (15)−0.0006 (12)0.0057 (11)−0.0011 (12)
C200.0159 (13)0.0149 (15)0.0136 (15)0.0020 (12)0.0069 (11)0.0005 (12)
Geometric parameters (Å, º) top
O1—C11.227 (3)C7—C81.395 (4)
O2—C11.307 (3)C7—H70.9500
O2—H2O0.846 (10)C8—C91.375 (4)
O3—C41.249 (3)C8—H80.9500
O4—C111.227 (3)C9—C101.401 (4)
O5—C111.305 (3)C9—H90.9500
O5—H5O0.857 (10)C10—H100.9500
O6—C141.247 (3)C11—C121.495 (4)
N1—C41.350 (3)C12—C131.344 (4)
N1—C51.419 (4)C12—H120.9500
N1—H1N0.879 (10)C13—C141.486 (4)
N2—C141.345 (4)C13—H130.9500
N2—C151.427 (4)C15—C201.391 (4)
N2—H2N0.886 (10)C15—C161.394 (4)
C1—C21.496 (4)C16—C171.379 (4)
C2—C31.335 (4)C16—H160.9500
C2—H20.9500C17—C181.394 (4)
C3—C41.476 (4)C17—H170.9500
C3—H30.9500C18—C191.389 (4)
C5—C101.387 (4)C18—H180.9500
C5—C61.403 (4)C19—C201.387 (4)
C6—C71.377 (4)C19—H190.9500
C6—H60.9500C20—H200.9500
C1—O2—H2O111 (3)C10—C9—H9119.7
C11—O5—H5O112 (2)C5—C10—C9119.3 (3)
C4—N1—C5128.0 (2)C5—C10—H10120.3
C4—N1—H1N114 (2)C9—C10—H10120.3
C5—N1—H1N118 (2)O4—C11—O5120.7 (2)
C14—N2—C15128.4 (2)O4—C11—C12118.0 (3)
C14—N2—H2N117 (2)O5—C11—C12121.3 (3)
C15—N2—H2N115 (2)C13—C12—C11132.0 (3)
O1—C1—O2121.2 (2)C13—C12—H12114.0
O1—C1—C2118.1 (2)C11—C12—H12114.0
O2—C1—C2120.7 (2)C12—C13—C14127.9 (2)
C3—C2—C1132.0 (3)C12—C13—H13116.0
C3—C2—H2114.0C14—C13—H13116.0
C1—C2—H2114.0O6—C14—N2123.0 (3)
C2—C3—C4128.4 (3)O6—C14—C13123.6 (3)
C2—C3—H3115.8N2—C14—C13113.4 (2)
C4—C3—H3115.8C20—C15—C16119.9 (3)
O3—C4—N1122.3 (3)C20—C15—N2123.9 (3)
O3—C4—C3123.1 (3)C16—C15—N2116.2 (2)
N1—C4—C3114.5 (2)C17—C16—C15119.7 (3)
C10—C5—C6119.8 (3)C17—C16—H16120.1
C10—C5—N1123.8 (2)C15—C16—H16120.1
C6—C5—N1116.4 (2)C16—C17—C18120.7 (3)
C7—C6—C5120.3 (3)C16—C17—H17119.6
C7—C6—H6119.8C18—C17—H17119.6
C5—C6—H6119.8C19—C18—C17119.4 (3)
C6—C7—C8119.9 (3)C19—C18—H18120.3
C6—C7—H7120.0C17—C18—H18120.3
C8—C7—H7120.0C20—C19—C18120.2 (3)
C9—C8—C7120.0 (3)C20—C19—H19119.9
C9—C8—H8120.0C18—C19—H19119.9
C7—C8—H8120.0C19—C20—C15120.1 (3)
C8—C9—C10120.6 (3)C19—C20—H20120.0
C8—C9—H9119.7C15—C20—H20120.0
O1—C1—C2—C3174.8 (3)O4—C11—C12—C13−175.7 (3)
O2—C1—C2—C3−5.1 (5)O5—C11—C12—C133.6 (5)
C1—C2—C3—C43.8 (5)C11—C12—C13—C14−5.2 (5)
C5—N1—C4—O32.6 (4)C15—N2—C14—O6−1.8 (5)
C5—N1—C4—C3−176.7 (3)C15—N2—C14—C13177.6 (2)
C2—C3—C4—O32.7 (5)C12—C13—C14—O6−1.1 (5)
C2—C3—C4—N1−178.0 (3)C12—C13—C14—N2179.4 (3)
C4—N1—C5—C10−9.5 (4)C14—N2—C15—C209.1 (4)
C4—N1—C5—C6171.4 (3)C14—N2—C15—C16−171.5 (3)
C10—C5—C6—C72.3 (4)C20—C15—C16—C17−0.4 (4)
N1—C5—C6—C7−178.5 (2)N2—C15—C16—C17−179.8 (2)
C5—C6—C7—C8−0.4 (4)C15—C16—C17—C18−0.6 (4)
C6—C7—C8—C9−1.2 (4)C16—C17—C18—C190.5 (4)
C7—C8—C9—C100.9 (4)C17—C18—C19—C200.5 (4)
C6—C5—C10—C9−2.5 (4)C18—C19—C20—C15−1.5 (4)
N1—C5—C10—C9178.4 (3)C16—C15—C20—C191.5 (4)
C8—C9—C10—C50.9 (4)N2—C15—C20—C19−179.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2o···O30.85 (1)1.63 (1)2.475 (3)172 (4)
O5—H5o···O60.86 (1)1.65 (1)2.496 (3)170 (3)
N1—H1n···O40.88 (1)2.00 (1)2.864 (3)166 (3)
N2—H2n···O1i0.89 (1)1.99 (1)2.859 (3)167 (3)
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC10H9NO3
Mr191.18
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)12.7505 (4), 10.5849 (5), 14.1918 (6)
β (°) 116.299 (3)
V (Å3)1717.1 (1)
Z8
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.24 × 0.06 × 0.06
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		11493, 3925, 2256
Rint0.062
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.208, 1.02
No. of reflections3925
No. of parameters269
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.96, −0.36

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2o···O30.85 (1)1.63 (1)2.475 (3)172 (4)
O5—H5o···O60.86 (1)1.65 (1)2.496 (3)170 (3)
N1—H1n···O40.88 (1)2.00 (1)2.864 (3)166 (3)
N2—H2n···O1i0.89 (1)1.99 (1)2.859 (3)167 (3)
Symmetry code: (i) x+1, y, z.
 

Acknowledgements

We thank the University of Malaya (FS339/2008 A) for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
 First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationGonzalez-Rodriguez, J., Canoira, L., Calderon, C. E., Martinez-Ripoll, M. & García Blanco, S. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 199–203.  Google Scholar
 First citationHome, S., Taylor, N., Colins, S. & Rodrigo, R. (1991). J. Chem. Soc. Perkin Trans. 1, pp. 3047–3051.  Google Scholar
 First citationLynch, D. E. & McClenaghan, I. (2002). Acta Cryst. E58, o678–o679.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationParvez, M., Shahid, K., Shahzadi, S. & Ali, S. (2004a). Acta Cryst. E60, o2079–o2081.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationParvez, M., Shahzadi, S., Shahid, K. & Ali, S. (2004b). Acta Cryst. E60, o2082–o2084.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationPrasad, S. M., Sinha, R. B. P., Mandal, D. K. & Rani, A. (2002a). Acta Cryst. E58, o1296–o1297.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationPrasad, S. M., Sinha, R. B. P., Mandal, D. K. & Rani, A. (2002b). Acta Cryst. E58, o891–o892.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSantos-Sánchez, N. F., Salas-Coronado, R., Peña-Hueso, A. & Flores-Parra, A. (2007). Acta Cryst. E63, o4156.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWardell, J. L., Skakle, J. M. S., Low, J. N. & Glidewell, C. (2005). Acta Cryst. E61, o3849–o3851.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 5| May 2009| Page o1101
doi:10.1107/S1600536809014627
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS