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

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ISSN: 2056-9890

Di­methyl 2-amino­bi­phenyl-4,4′-di­carboxyl­ate

aDepartment of Chemistry and Biochemistry, University of Massachusetts Dartmouth, 285 Old Westport Road, North Dartmouth, MA 02747, USA, and bDepartment of Chemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
*Correspondence e-mail: dmanke@umassd.edu

(Received 9 April 2013; accepted 19 April 2013; online 27 April 2013)

The title compound, C16H15NO4, exhibits two near-planar aromatic ester groups with a maximum aryl–ester torsion angle of 1.9 (2)°. The dihedral angle between the benzene rings is 44.7 (1)°. In the crystal, N—H⋯O hydrogen bonding is observed along with C—H⋯O contacts, forming chanins along [101]. No ππ inter­actions were noted between the benzene rings.

Related literature

For the synthesis of the title compound, see: Olkhovik et al. (2008[Olkhovik, V. K., Vasilevskii, D. A., Pap, A. A., Kalechyts, G. V., Matveienko, Y. V., Baran, A. G., Halinouski, N. A. & Petushok, V. G. (2008). ARKIVOC, pp. 69-93.]). For the crystal structures of the parent dimethyl-4,4′-di­carboxyl­ate and its structurally characterized amino derivatives, see: Ritzerfeld et al. (2009[Ritzerfeld, V., Pyrlik, A., Wang, Y. & Englert, U. (2009). Acta Cryst. E65, o1677.]); Nyburg et al. (1988[Nyburg, S. C., Prasad, L., Behnam, B. A. & Hall, D. M. (1988). J. Chem. Soc. Perkin Trans. 2, pp. 617-623.]). For metal-organic framework structures with this and related linkers, see: Deshpande et al. (2010[Deshpande, R. K., Minnaar, J. L. & Telfer, S. G. (2010). Angew. Chem. Int. Ed. 49, 4598-4602.]); Lun et al. (2011[Lun, D. J., Waterhouse, G. I. N. & Telfer, S. G. (2011). J. Am. Chem. Soc. 133, 5806-5809.]); Gupta et al. (2012[Gupta, A. S., Deshpande, R. K., Liu, L., Waterhouse, G. I. N. & Telfer, S. G. (2012). CrystEngComm, 14, 5701-5704.]); Sudik et al. (2005[Sudik, A. D., Millward, A. R., Ockwig, N. W., Cote, A. P., Kim, J. & Yaghi, O. M. (2005). J. Am. Chem. Soc. 127, 7110-7118.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15NO4

  • Mr = 285.29

  • Monoclinic, P 21 /c

  • a = 12.955 (3) Å

  • b = 7.3460 (16) Å

  • c = 14.422 (3) Å

  • β = 103.263 (10)°

  • V = 1336.0 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 90 K

  • 0.28 × 0.12 × 0.06 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.972, Tmax = 0.994

  • 9113 measured reflections

  • 2463 independent reflections

  • 1785 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.124

  • S = 1.01

  • 2463 reflections

  • 198 parameters

  • 2 restraints

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

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1NB⋯O2i 0.88 (1) 2.54 (2) 3.304 (3) 146 (2)
N1—H1NA⋯O4ii 0.88 (1) 2.33 (1) 3.147 (2) 155 (2)
C4—H4A⋯O2i 0.95 2.44 3.301 (3) 150
Symmetry codes: (i) -x, -y+2, -z; (ii) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Biphenyl-4,4'-dicarboxylate and its derivatives are widely used in metal-organic (MOFs) frameworks as linkers (Sudik et al. 2005). One of the many advantages of MOFs is the ability to incorporate different functional groups within their pores. An area of interest is the inclusion of open Lewis base sites on the interior surfaces of MOFs. As a part of our efforts in this field, we prepared the previously reported dimethyl-2-aminobiphenyl-4,4'-dicarboxylate (Olkhovik et al. 2008) and report its structure herein.

The molecular structure of the title compound is shown in Figure 1. The two phenyl rings demonstrate a dihedral angle of 135.3°. In the crystal, intermolecular hydrogen bonding is observed between N1–H1NA···O4 and N1H1NB···O2. There is also a close C–H···O contact along C4H4A···O2. No π-π interactions were noted between the phenyl rings. The packing for the title compound indicating hydrogen bonding is shown in Figure 2.

Related literature top

For the synthesis of the title compound, see: Olkhovik et al. (2008). For the crystal structures of the parent dimethyl-4,4'-dicarboxylate and its structurally characterized amino derivatives, see: Ritzerfeld et al. (2009); Nyburg et al. (1988). For metal-organic framework structures with this and related linkers, see: Deshpande et al. (2010); Lun et al. (2011); Gupta et al. (2012); Sudik et al. (2005).

Experimental top

The compound was prepared by literature procedure (Olkhovik et al. 2008). Crystals suitable for single-crystal X-ray analysis were grown by slow evaporation of an ethanol solution.

Refinement top

All non-hydrogen atoms were refined anisotropically (SHELXL) by full matrix least squares on F2. Hydrogen atoms H1NA and H1NB were found from a Fourier difference map and were refined with fixed distance of 0.87 (005) Å and isotropic displacement parameter of 1.20 times Ueq of parent N atom. All other hydrogen atoms were placed in calculated positions and then refined with riding model with C—H lengths of 0.95 Å for (CH) and 0.98 Å for (CH3) and with isotropic displacement parameters set to 1.20 and 1.50 times Ueq of the parent C atom.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as spheres of arbitrary radius.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
Dimethyl 2-aminobiphenyl-4,4'-dicarboxylate top
Crystal data top
C16H15NO4F(000) = 600
Mr = 285.29Dx = 1.418 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2401 reflections
a = 12.955 (3) Åθ = 2.9–24.9°
b = 7.3460 (16) ŵ = 0.10 mm1
c = 14.422 (3) ÅT = 90 K
β = 103.263 (10)°Plate, colourless
V = 1336.0 (5) Å30.28 × 0.12 × 0.06 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
2463 independent reflections
Radiation source: fine-focus sealed tube1785 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ϕ and ω scansθmax = 25.5°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1515
Tmin = 0.972, Tmax = 0.994k = 88
9113 measured reflectionsl = 1717
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0609P)2 + 0.6328P]
where P = (Fo2 + 2Fc2)/3
2463 reflections(Δ/σ)max < 0.001
198 parametersΔρmax = 0.27 e Å3
2 restraintsΔρmin = 0.35 e Å3
Crystal data top
C16H15NO4V = 1336.0 (5) Å3
Mr = 285.29Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.955 (3) ŵ = 0.10 mm1
b = 7.3460 (16) ÅT = 90 K
c = 14.422 (3) Å0.28 × 0.12 × 0.06 mm
β = 103.263 (10)°
Data collection top
Bruker APEXII CCD
diffractometer
2463 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
1785 reflections with I > 2σ(I)
Tmin = 0.972, Tmax = 0.994Rint = 0.036
9113 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0452 restraints
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.27 e Å3
2463 reflectionsΔρmin = 0.35 e Å3
198 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
O10.06313 (12)0.5135 (2)0.10419 (10)0.0276 (4)
O20.00179 (13)0.7915 (2)0.09219 (11)0.0351 (4)
O30.71122 (11)0.6353 (2)0.53463 (9)0.0237 (4)
O40.61240 (12)0.7629 (2)0.62568 (10)0.0280 (4)
N10.22094 (16)1.0226 (3)0.21975 (14)0.0321 (5)
H1NB0.1839 (17)1.109 (2)0.1855 (15)0.038*
H1NA0.2785 (12)1.051 (3)0.2629 (13)0.038*
C10.00925 (17)0.4946 (3)0.19589 (14)0.0277 (5)
H1C0.01220.36680.21570.042*
H1B0.01530.56950.24280.042*
H1A0.08010.53490.19150.042*
C20.06020 (17)0.6717 (3)0.05967 (15)0.0215 (5)
C30.14017 (16)0.6815 (3)0.03194 (14)0.0201 (5)
C40.14580 (16)0.8404 (3)0.08492 (14)0.0205 (5)
H4A0.09760.93670.06240.025*
C50.22104 (16)0.8614 (3)0.17076 (14)0.0190 (5)
C60.29167 (16)0.7167 (3)0.20412 (14)0.0181 (5)
C70.28276 (16)0.5577 (3)0.14953 (14)0.0206 (5)
H7A0.32940.45920.17190.025*
C80.20895 (17)0.5381 (3)0.06445 (14)0.0212 (5)
H8A0.20520.42860.02870.025*
C90.37584 (16)0.7249 (3)0.29319 (14)0.0188 (5)
C100.35757 (16)0.7869 (3)0.37973 (14)0.0198 (5)
H10A0.28990.83390.38190.024*
C110.43708 (17)0.7805 (3)0.46212 (14)0.0209 (5)
H11A0.42350.82290.52040.025*
C120.53657 (16)0.7127 (3)0.46029 (14)0.0188 (5)
C130.55552 (17)0.6511 (3)0.37448 (14)0.0211 (5)
H13A0.62330.60400.37250.025*
C140.47657 (16)0.6582 (3)0.29247 (14)0.0215 (5)
H14A0.49090.61700.23420.026*
C150.62115 (16)0.7076 (3)0.54930 (15)0.0198 (5)
C160.79774 (17)0.6225 (3)0.61760 (15)0.0258 (5)
H16A0.85900.56600.59990.039*
H16B0.77600.54800.66620.039*
H16C0.81700.74460.64310.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0266 (9)0.0302 (9)0.0209 (8)0.0058 (7)0.0052 (7)0.0085 (7)
O20.0427 (10)0.0261 (9)0.0284 (9)0.0092 (8)0.0087 (8)0.0008 (7)
O30.0201 (8)0.0284 (8)0.0188 (8)0.0022 (7)0.0030 (6)0.0014 (6)
O40.0283 (9)0.0359 (9)0.0183 (8)0.0000 (7)0.0019 (7)0.0053 (7)
N10.0321 (12)0.0302 (11)0.0304 (12)0.0010 (9)0.0001 (9)0.0020 (9)
C10.0267 (12)0.0343 (13)0.0168 (11)0.0013 (10)0.0059 (9)0.0066 (9)
C20.0238 (11)0.0199 (11)0.0203 (11)0.0008 (9)0.0038 (9)0.0003 (9)
C30.0204 (11)0.0224 (11)0.0171 (11)0.0025 (9)0.0033 (9)0.0003 (9)
C40.0203 (11)0.0193 (10)0.0213 (11)0.0015 (9)0.0035 (9)0.0018 (9)
C50.0204 (11)0.0201 (11)0.0175 (10)0.0030 (9)0.0062 (9)0.0013 (9)
C60.0166 (10)0.0229 (11)0.0155 (10)0.0017 (9)0.0052 (9)0.0000 (8)
C70.0196 (11)0.0210 (11)0.0205 (11)0.0022 (9)0.0032 (9)0.0002 (9)
C80.0234 (11)0.0201 (11)0.0197 (11)0.0001 (9)0.0037 (9)0.0026 (9)
C90.0209 (11)0.0168 (10)0.0176 (10)0.0035 (9)0.0019 (9)0.0006 (8)
C100.0191 (11)0.0207 (11)0.0191 (11)0.0001 (9)0.0036 (9)0.0021 (9)
C110.0251 (12)0.0202 (11)0.0177 (11)0.0001 (9)0.0055 (9)0.0028 (8)
C120.0205 (11)0.0163 (10)0.0181 (11)0.0032 (9)0.0014 (9)0.0014 (8)
C130.0187 (11)0.0243 (12)0.0202 (11)0.0001 (9)0.0044 (9)0.0008 (9)
C140.0218 (11)0.0274 (12)0.0162 (10)0.0021 (9)0.0060 (9)0.0048 (9)
C150.0227 (12)0.0151 (10)0.0204 (11)0.0042 (9)0.0023 (9)0.0021 (9)
C160.0220 (12)0.0291 (12)0.0216 (11)0.0012 (10)0.0047 (9)0.0014 (10)
Geometric parameters (Å, º) top
O1—C21.332 (2)C6—C91.483 (3)
O1—C11.442 (2)C7—C81.379 (3)
O2—C21.211 (2)C7—H7A0.9500
O3—C151.342 (2)C8—H8A0.9500
O3—C161.443 (2)C9—C141.396 (3)
O4—C151.204 (2)C9—C101.399 (3)
N1—C51.379 (3)C10—C111.383 (3)
N1—H1NB0.877 (5)C10—H10A0.9500
N1—H1NA0.879 (5)C11—C121.388 (3)
C1—H1C0.9800C11—H11A0.9500
C1—H1B0.9800C12—C131.391 (3)
C1—H1A0.9800C12—C151.485 (3)
C2—C31.482 (3)C13—C141.376 (3)
C3—C41.388 (3)C13—H13A0.9500
C3—C81.390 (3)C14—H14A0.9500
C4—C51.397 (3)C16—H16A0.9800
C4—H4A0.9500C16—H16B0.9800
C5—C61.413 (3)C16—H16C0.9800
C6—C71.399 (3)
C2—O1—C1116.20 (16)C7—C8—H8A120.6
C15—O3—C16115.67 (16)C3—C8—H8A120.6
C5—N1—H1NB113.4 (17)C14—C9—C10118.07 (19)
C5—N1—H1NA117.6 (17)C14—C9—C6118.81 (18)
H1NB—N1—H1NA120 (2)C10—C9—C6123.01 (19)
O1—C1—H1C109.5C11—C10—C9120.68 (19)
O1—C1—H1B109.5C11—C10—H10A119.7
H1C—C1—H1B109.5C9—C10—H10A119.7
O1—C1—H1A109.5C10—C11—C12120.51 (18)
H1C—C1—H1A109.5C10—C11—H11A119.7
H1B—C1—H1A109.5C12—C11—H11A119.7
O2—C2—O1122.46 (19)C11—C12—C13119.20 (19)
O2—C2—C3125.17 (19)C11—C12—C15119.80 (18)
O1—C2—C3112.37 (17)C13—C12—C15121.00 (19)
C4—C3—C8120.21 (18)C14—C13—C12120.3 (2)
C4—C3—C2117.99 (18)C14—C13—H13A119.9
C8—C3—C2121.80 (18)C12—C13—H13A119.9
C3—C4—C5121.22 (19)C13—C14—C9121.25 (18)
C3—C4—H4A119.4C13—C14—H14A119.4
C5—C4—H4A119.4C9—C14—H14A119.4
N1—C5—C4117.78 (19)O4—C15—O3123.07 (19)
N1—C5—C6123.24 (18)O4—C15—C12125.2 (2)
C4—C5—C6118.97 (18)O3—C15—C12111.68 (17)
C7—C6—C5118.25 (18)O3—C16—H16A109.5
C7—C6—C9118.09 (18)O3—C16—H16B109.5
C5—C6—C9123.65 (18)H16A—C16—H16B109.5
C8—C7—C6122.60 (19)O3—C16—H16C109.5
C8—C7—H7A118.7H16A—C16—H16C109.5
C6—C7—H7A118.7H16B—C16—H16C109.5
C7—C8—C3118.75 (19)
C1—O1—C2—O22.4 (3)C5—C6—C9—C14136.4 (2)
C1—O1—C2—C3177.63 (17)C7—C6—C9—C10133.4 (2)
O2—C2—C3—C40.5 (3)C5—C6—C9—C1047.5 (3)
O1—C2—C3—C4179.46 (17)C14—C9—C10—C110.5 (3)
O2—C2—C3—C8179.8 (2)C6—C9—C10—C11175.68 (19)
O1—C2—C3—C80.2 (3)C9—C10—C11—C120.1 (3)
C8—C3—C4—C51.0 (3)C10—C11—C12—C130.0 (3)
C2—C3—C4—C5178.30 (18)C10—C11—C12—C15179.73 (18)
C3—C4—C5—N1179.38 (19)C11—C12—C13—C140.3 (3)
C3—C4—C5—C60.6 (3)C15—C12—C13—C14179.44 (18)
N1—C5—C6—C7178.43 (19)C12—C13—C14—C90.7 (3)
C4—C5—C6—C70.2 (3)C10—C9—C14—C130.8 (3)
N1—C5—C6—C92.5 (3)C6—C9—C14—C13175.55 (18)
C4—C5—C6—C9178.85 (18)C16—O3—C15—O41.7 (3)
C5—C6—C7—C80.8 (3)C16—O3—C15—C12179.20 (16)
C9—C6—C7—C8178.35 (19)C11—C12—C15—O42.0 (3)
C6—C7—C8—C30.5 (3)C13—C12—C15—O4177.7 (2)
C4—C3—C8—C70.4 (3)C11—C12—C15—O3178.96 (18)
C2—C3—C8—C7178.82 (19)C13—C12—C15—O31.3 (3)
C7—C6—C9—C1442.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1NB···O2i0.88 (1)2.54 (2)3.304 (3)146 (2)
N1—H1NA···O4ii0.88 (1)2.33 (1)3.147 (2)155 (2)
C4—H4A···O2i0.952.443.301 (3)150
Symmetry codes: (i) x, y+2, z; (ii) x+1, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC16H15NO4
Mr285.29
Crystal system, space groupMonoclinic, P21/c
Temperature (K)90
a, b, c (Å)12.955 (3), 7.3460 (16), 14.422 (3)
β (°) 103.263 (10)
V3)1336.0 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.28 × 0.12 × 0.06
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.972, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections
9113, 2463, 1785
Rint0.036
(sin θ/λ)max1)0.607
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.124, 1.01
No. of reflections2463
No. of parameters198
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.35

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1NB···O2i0.877 (5)2.541 (15)3.304 (3)146 (2)
N1—H1NA···O4ii0.879 (5)2.328 (12)3.147 (2)155 (2)
C4—H4A···O2i0.952.443.301 (3)150.4
Symmetry codes: (i) x, y+2, z; (ii) x+1, y+2, z+1.
 

Acknowledgements

RLL thanks the Jean Dreyfus Boissevain Lectureship for Undergraduate Institutions, the UMass Dartmouth Office of Undergraduate Research Award and the UMass Dartmouth Honors Summer Research Grant for funding. DRM gratefully acknowledges support from the UMass Dartmouth Chancellor's Research Fund and the Joseph P. Healey Endowment.

References

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