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

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catena-Poly[{μ3-3,3′-[(1,7-dioxa-4,10-di­aza­cyclo­do­decane-4,10-di­yl)bis­­(methyl­ene)]dibenzoato}cobalt(II)]

aCenter for Functional Nanoscale Materials, Department of Chemistry, Clark Atlanta University, 223 James P. Brawley Drive, Atlanta, GA 30314, USA, and bX-ray Crystallography Center, Emory University, Atlanta, GA 30322, USA
*Correspondence e-mail: cingram@cau.edu

(Received 26 September 2013; accepted 3 December 2013; online 18 December 2013)

The title compound, [Co(C24H28N2O6)]n, crystallizes as infinite chains related to one another by inversion centers, giving a centrosymmetric coordination polymer. The CoII ion, situated on a twofold rotation axis, forms a complex with the crown-4 moiety of the 3,3′-[(1,7-dioxa-4,10-di­aza­cyclo­do­decane-4,10-di­yl)bis­(meth­ylene)]dibenzoate anion. The dis­torted octahedral coordination sphere of the CoII ion is completed by two carboxyl­ate O atoms from two bridging intra-chain ligands. Metallomacrocyclic rings of 16 atoms are present, with each ring containing two CoII ions and 14 atoms from the bridging ligands. These units repeat as infinite zigzag chains along [101].

Related literature

For the structures of coordination polymers (CPs) or compounds with metal-organic frameworks including one-dimensional CPs or MOFs, see: Du et al. (2013[Du, M., Li, C. P., Liu, C. S. & Fang, S. M. (2013). Coord. Chem. Rev. 257, 1282-1305.]); Ingram et al. (2012[Ingram, C. W., Liao, L. & Bacsa, J. (2012). Acta Cryst. E68, m1410.], 2013[Ingram, C. W., Liao, L., Bacsa, J., Harruna, I., Sabo, D. & Zhang, Z. J. (2013). Cryst. Growth Des. 13, 1131-1139.]); Janiak (2013[Janiak, C. (2013). Chem. Commun. 49, 6933-6937.]); Leong & Vittal (2011[Leong, W. L. & Vittal, J. J. (2011). Chem. Rev. 111, 688-764.]).

[Scheme 1]

Experimental

Crystal data
  • [Co(C24H28N2O6)]

  • Mr = 499.41

  • Monoclinic, C 2/c

  • a = 20.626 (2) Å

  • b = 8.9778 (10) Å

  • c = 13.9263 (16) Å

  • β = 127.051 (1)°

  • V = 2058.2 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.88 mm−1

  • T = 173 K

  • 0.40 × 0.14 × 0.14 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2012)[Bruker (2012). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.] Tmin = 0.606, Tmax = 0.746

  • 3614 measured reflections

  • 2930 independent reflections

  • 2290 reflections with I > 2σ(I)

  • Rint = 0.018

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.125

  • S = 1.02

  • 2930 reflections

  • 150 parameters

  • H-atom parameters constrained

  • Δρmax = 0.80 e Å−3

  • Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.

Supporting information


Comment top

The title compound is the one of a series of coordination polymers prepared from the anionic ligand LH2, 3,3'-((1,7-dioxa-4,10-diazacyclododecane-4,10-diyl)bis(methylene))dibenzoate. This ligand shows unusual adaptability in that it displays two complexation modes on binding to metals. The ligand attaches to the metal via two oxygen and two nitrogen atoms (forming a crown complex). The crown forms four bonds to the metal, while an ideal coordination number for a CoII ion is 6. Thus vacant coordination sites suitable for coordination by the carboxylate groups exist. The carboxylate ions behave as monodentate bridging ligands and the entire ligand is hexadentate. The CoII atom is moved out of the best plane of the crown since this arrangement is better for forming optimal bonds to the ligand. This new compound is novel in that, although the ligands bridge the metal atoms forming one-dimensional chains, the metal atoms are positioned in the center of the organic linker. Topologically, the CoII atoms and the ligands forms nodes in the network rather than the metal atoms only.

The title compound is synthesized from the ligand LH2, 3,3'-((1,7-dioxa-4,10-diazacyclododecane-4,10-diyl)bis(methylene)) dibenzoic acid. The metal atoms are positioned in the center of the organic linker. The asymmetric unit of the compound contains a CoII ion and a deprotonated ligand L with formula C24H28N2O6Co. The CoII ion is 6-coordinate in a distorted octahedral geometry being bound to two N atoms and two O atoms of the crown (1,7-diaza-12-crown-4) and two carboxylic O atoms, one from each of two additional intra-chain ligands (Figure 1s). The Co1—O1, Co1—O3 and Co1—N1 bond lengths are 1.9886 (16), 2.2399 (16) and 2.2213 (17) Å, respectively. The O1—Co1—O1 angle is 104.15 (9)°. The shortest distance between two neighboring CoII ions along a chain is 9.046 (1) Å. The CoII ion of the Co(crown-4)2+ unit is located on a 2-fold rotation axis. The symmetry independent atoms consist of one half of the ligand with the rotation axis generating the second half of the ligand at the Co atom. Bond circuits consisting of sixteen-membered metallomacrocycle rings can be identified in the structure. Each ring contains two CoII ions and fourteen non-H atoms of the ligand. Each CoII ion is a node for three ligands and two connected macrocycle rings. The pair of benzene moieties within a metallomacrocycle ring are remarkably co-planar (the two rings are in the same plane within experimental error). The dihedral angle between this plane and the plane of the next two nearest phenyl rings along the 1-D chain is 68.79 (5)°. Repetition of these units creates a 1-D polymer network with an infinite number of these rings.

Related literature top

For the structures of coordination polymers (CPs) or compounds with metal-organic frameworks including one-dimensional CPs or MOFs, see: Du et al. (2013); Ingram et al. (2012, 2013); Janiak (2013); Leong & Vittal (2011).

Experimental top

The title compound was synthesized in an autoclave by mixing the ligand, 3,3'-((1,7-dioxa-4,10-diazacyclododecane-4,10-diyl)bis(methylene))dibenzoic acid, LH2 (4x10-5 mol), (Ingram et al. (2012), (2013)) Co(NO3)2·6H2O (1.2x10-4 mol, 35.8 mg), H2O (12 ml) and pyridine (4x10-2 ml). The mixture was heated at 130 °C in an autoclave for 7 days and then cooled to ambient temperature. Red crystals were collected and washed with H2O by filtration. Elem. anal. calcd. C24H28N2O6Co %: C, 57.72; H, 5.65; N, 5.61; Found: C, 57.79; H, 5.74; N, 5.46.

Refinement top

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 > 2sigma(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. Computing details Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009);program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. A view of a portion of one of the chains of (I). Non-H atoms are represented by ellipsoids at the 50% probability level. Sixteen membered metallomacrocycle rings can be identified from this figure.
catena-Poly[{µ3-3,3'-[(1,7-dioxa-4,10-diazacyclododecane-4,10-diyl)bis(methylene)]dibenzoato}cobalt(II)] top
Crystal data top
[Co(C24H28N2O6)]F(000) = 1044
Mr = 499.41Dx = 1.612 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 20.626 (2) ÅCell parameters from 4901 reflections
b = 8.9778 (10) Åθ = 2.5–31.0°
c = 13.9263 (16) ŵ = 0.88 mm1
β = 127.051 (1)°T = 173 K
V = 2058.2 (4) Å3Needle, red
Z = 40.40 × 0.14 × 0.14 mm
Data collection top
Bruker D8
diffractometer with a APEXII detector
2930 independent reflections
Radiation source: fine-focus sealed tube2290 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
Detector resolution: 512 pixels mm-1θmax = 31.2°, θmin = 2.6°
ϕ and ω scans with a narrow frame widthh = 2818
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
k = 124
Tmin = 0.606, Tmax = 0.746l = 2019
3614 measured reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: difference Fourier map
wR(F2) = 0.125H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.073P)2]
where P = (Fo2 + 2Fc2)/3
2930 reflections(Δ/σ)max < 0.001
150 parametersΔρmax = 0.80 e Å3
0 restraintsΔρmin = 0.47 e Å3
Crystal data top
[Co(C24H28N2O6)]V = 2058.2 (4) Å3
Mr = 499.41Z = 4
Monoclinic, C2/cMo Kα radiation
a = 20.626 (2) ŵ = 0.88 mm1
b = 8.9778 (10) ÅT = 173 K
c = 13.9263 (16) Å0.40 × 0.14 × 0.14 mm
β = 127.051 (1)°
Data collection top
Bruker D8
diffractometer with a APEXII detector
2930 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
2290 reflections with I > 2σ(I)
Tmin = 0.606, Tmax = 0.746Rint = 0.018
3614 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.125H-atom parameters constrained
S = 1.02Δρmax = 0.80 e Å3
2930 reflectionsΔρmin = 0.47 e Å3
150 parameters
Special details top

Experimental. Absorption correction: SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0566 before and 0.0407 after correction. The Ratio of minimum to maximum transmission is 0.8118. The λ/2 correction factor is 0.0015.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
H30.21310.18610.39610.018*
H50.32140.05510.28580.021*
H60.19620.09220.10300.020*
H70.07990.00630.06560.017*
H8a0.35370.17440.52420.018*
H8b0.39960.13150.47080.018*
H9a0.31260.01660.59360.022*
H9b0.29550.14750.50680.022*
H10a0.33430.23060.69860.025*
H10b0.38900.29840.66560.025*
H11a0.47550.28830.91280.023*
H11b0.51710.31170.84920.023*
H12a0.38330.21320.46730.022*
H12b0.44230.09400.47680.022*
C10.06017 (14)0.1928 (2)0.19467 (19)0.0158 (4)
C20.13474 (13)0.1115 (2)0.22645 (18)0.0134 (4)
C30.20986 (14)0.1300 (2)0.33718 (19)0.0148 (4)
C40.28076 (14)0.0671 (2)0.36296 (18)0.0139 (4)
C50.27494 (14)0.0150 (3)0.27221 (19)0.0174 (5)
C60.19972 (15)0.0363 (2)0.16222 (19)0.0171 (4)
C70.12995 (14)0.0239 (2)0.13905 (19)0.0143 (4)
C80.36136 (14)0.0955 (2)0.48429 (19)0.0153 (4)
C90.33771 (14)0.0978 (3)0.5810 (2)0.0185 (5)
C100.37353 (14)0.2069 (3)0.6840 (2)0.0205 (5)
C110.50015 (14)0.2376 (2)0.8806 (2)0.0194 (5)
C120.42768 (14)0.1462 (2)0.52219 (19)0.0184 (5)
N10.39880 (11)0.03569 (18)0.56797 (16)0.0130 (4)
O10.07535 (10)0.31870 (17)0.24829 (14)0.0177 (3)
O20.00750 (10)0.1403 (2)0.11880 (15)0.0266 (4)
O30.44337 (10)0.13620 (18)0.78732 (13)0.0184 (3)
Co10.00000.45483 (4)0.25000.01262 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0172 (12)0.0174 (10)0.0141 (9)0.0039 (8)0.0102 (9)0.0025 (8)
C20.0121 (11)0.0108 (9)0.0152 (9)0.0006 (7)0.0070 (8)0.0018 (7)
C30.0175 (11)0.0117 (9)0.0141 (9)0.0000 (8)0.0090 (9)0.0014 (7)
C40.0128 (11)0.0142 (10)0.0121 (9)0.0002 (7)0.0062 (8)0.0003 (7)
C50.0153 (12)0.0193 (11)0.0161 (10)0.0031 (8)0.0086 (9)0.0003 (8)
C60.0205 (12)0.0151 (10)0.0148 (9)0.0033 (8)0.0103 (9)0.0013 (8)
C70.0138 (11)0.0138 (10)0.0120 (9)0.0012 (8)0.0060 (8)0.0005 (7)
C80.0132 (11)0.0135 (9)0.0154 (9)0.0002 (8)0.0066 (9)0.0007 (7)
C90.0120 (11)0.0204 (11)0.0165 (10)0.0034 (8)0.0052 (9)0.0006 (8)
C100.0167 (12)0.0202 (11)0.0181 (10)0.0061 (9)0.0071 (9)0.0003 (8)
C110.0162 (12)0.0169 (11)0.0178 (10)0.0027 (8)0.0064 (9)0.0049 (8)
C120.0178 (12)0.0175 (10)0.0153 (9)0.0032 (8)0.0075 (9)0.0035 (8)
N10.0104 (9)0.0122 (8)0.0139 (8)0.0011 (6)0.0059 (7)0.0004 (6)
O10.0156 (8)0.0148 (7)0.0219 (8)0.0001 (6)0.0110 (7)0.0024 (6)
O20.0132 (9)0.0302 (10)0.0244 (8)0.0007 (7)0.0049 (7)0.0103 (7)
O30.0140 (8)0.0165 (7)0.0152 (7)0.0027 (6)0.0037 (6)0.0016 (6)
Co10.0105 (2)0.0114 (2)0.0141 (2)0.0000.00639 (17)0.000
Geometric parameters (Å, º) top
C1—C21.508 (3)C11—H11b0.9700
C2—C31.388 (3)C11—C12i1.515 (3)
C2—C71.402 (3)C12—H12a0.9700
C3—H30.9300C12—H12b0.9700
C4—C31.398 (3)C12—C11i1.515 (3)
C4—C81.516 (3)N1—C81.502 (3)
C5—H50.9300N1—C91.486 (3)
C5—C41.404 (3)N1—C121.484 (3)
C6—H60.9300N1—Co1ii2.2212 (17)
C6—C51.388 (3)O1—C11.285 (3)
C7—H70.9300O2—C11.229 (3)
C7—C61.381 (3)O3—C101.432 (3)
C8—H8a0.9700O3—C111.433 (3)
C8—H8b0.9700O3—Co1ii2.2400 (16)
C9—H9a0.9700Co1—N1iii2.2213 (17)
C9—H9b0.9700Co1—N1ii2.2213 (17)
C9—C101.511 (3)Co1—O11.9886 (16)
C10—H10a0.9700Co1—O1iv1.9886 (16)
C10—H10b0.9700Co1—O3iii2.2399 (16)
C11—H11a0.9700Co1—O3ii2.2399 (16)
O1—C1—C2114.0 (2)O3—C10—C9106.67 (18)
O2—C1—C2119.75 (19)H11a—C11—H11b108.6
O2—C1—O1126.2 (2)C12i—C11—H11a110.3
C3—C2—C1121.76 (19)C12i—C11—H11b110.3
C3—C2—C7118.7 (2)O3—C11—H11a110.3
C7—C2—C1119.40 (19)O3—C11—H11b110.3
C2—C3—H3118.9O3—C11—C12i107.00 (17)
C2—C3—C4122.10 (19)H12a—C12—H12b107.6
C4—C3—H3118.9C11i—C12—H12a108.7
C3—C4—C5118.2 (2)C11i—C12—H12b108.7
C3—C4—C8119.56 (19)N1—C12—H12a108.7
C5—C4—C8122.2 (2)N1—C12—H12b108.7
C4—C5—H5120.1N1—C12—C11i114.25 (17)
C6—C5—H5120.1C8—N1—Co1ii108.63 (12)
C6—C5—C4119.9 (2)C9—N1—C8108.17 (17)
C5—C6—H6119.4C9—N1—Co1ii105.43 (12)
C7—C6—H6119.4C12—N1—C8110.02 (17)
C7—C6—C5121.2 (2)C12—N1—C9113.03 (17)
C2—C7—H7120.1C12—N1—Co1ii111.36 (13)
C6—C7—H7120.1C1—O1—Co1128.97 (15)
C6—C7—C2119.9 (2)C10—O3—C11114.03 (17)
H8a—C8—H8b107.4C10—O3—Co1ii116.01 (13)
C4—C8—H8a108.3C11—O3—Co1ii114.60 (13)
C4—C8—H8b108.3N1iii—Co1—N1ii141.85 (9)
N1—C8—H8a108.3N1iii—Co1—O3iii76.37 (6)
N1—C8—H8b108.3N1ii—Co1—O3iii76.14 (6)
N1—C8—C4116.03 (17)N1ii—Co1—O3ii76.37 (6)
H9a—C9—H9b107.8N1iii—Co1—O3ii76.14 (6)
C10—C9—H9a108.9O1—Co1—N1ii90.61 (7)
C10—C9—H9b108.9O1iv—Co1—N1ii113.02 (7)
N1—C9—H9a108.9O1iv—Co1—N1iii90.61 (7)
N1—C9—H9b108.9O1—Co1—N1iii113.02 (7)
N1—C9—C10113.18 (19)O1iv—Co1—O1104.15 (9)
H10b—C10—H10a108.6O1—Co1—O3ii85.61 (6)
C9—C10—H10a110.4O1iv—Co1—O3iii85.61 (6)
C9—C10—H10b110.4O1—Co1—O3iii165.96 (6)
O3—C10—H10a110.4O1iv—Co1—O3ii165.96 (6)
O3—C10—H10b110.4O3iii—Co1—O3ii86.74 (9)
C1—C2—C3—C4173.4 (2)C10—O3—C11—C12i175.92 (19)
C1—C2—C7—C6172.2 (2)C11—O3—C10—C9159.56 (19)
C2—C7—C6—C51.7 (3)C12—N1—C8—C470.1 (2)
C3—C2—C7—C62.9 (3)C12—N1—C9—C1071.2 (2)
C3—C4—C8—N1110.1 (2)N1—C9—C10—O349.7 (3)
C5—C4—C3—C21.1 (3)O1—C1—C2—C328.4 (3)
C5—C4—C8—N173.0 (3)O1—C1—C2—C7146.5 (2)
C6—C5—C4—C32.4 (3)O2—C1—C2—C3155.1 (2)
C6—C5—C4—C8179.3 (2)O2—C1—C2—C730.0 (3)
C7—C2—C3—C41.5 (3)Co1ii—N1—C8—C4167.72 (15)
C7—C6—C5—C41.0 (3)Co1ii—N1—C9—C1050.7 (2)
C8—C4—C3—C2178.10 (19)Co1ii—N1—C12—C11i30.1 (2)
C8—N1—C9—C10166.73 (18)Co1—O1—C1—C2172.68 (13)
C8—N1—C12—C11i150.6 (2)Co1—O1—C1—O211.1 (3)
C9—N1—C8—C453.8 (2)Co1ii—O3—C10—C923.1 (2)
C9—N1—C12—C11i88.3 (2)Co1ii—O3—C11—C12i38.8 (2)
Symmetry codes: (i) x+1, y, z+3/2; (ii) x+1/2, y1/2, z+1; (iii) x1/2, y1/2, z1/2; (iv) x, y, z+1/2.

Experimental details

Crystal data
Chemical formula[Co(C24H28N2O6)]
Mr499.41
Crystal system, space groupMonoclinic, C2/c
Temperature (K)173
a, b, c (Å)20.626 (2), 8.9778 (10), 13.9263 (16)
β (°) 127.051 (1)
V3)2058.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.88
Crystal size (mm)0.40 × 0.14 × 0.14
Data collection
DiffractometerBruker D8
diffractometer with a APEXII detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2012)
Tmin, Tmax0.606, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
3614, 2930, 2290
Rint0.018
(sin θ/λ)max1)0.729
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.125, 1.02
No. of reflections2930
No. of parameters150
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.80, 0.47

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

 

Acknowledgements

Financial support of NSF/CREST/ CFNM (award No. HRD-1137751) is acknowledged.

References

First citationBruker (2009). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2012). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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