3-(2-Acetyl­anilino)propanoic acid

Sparrow, C.R.; Walker, E.H. Jr; Fronczek, F.R.

doi:10.1107/S1600536808035277

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2359

doi:10.1107/S1600536808035277

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3-(2-Acetylanilino)propanoic acid

Christopher R. Sparrow,^a Edwin H. Walker Jr ^a and Frank R. Fronczek ^b ^*

^aDepartment of Chemistry, Southern University, Baton Rouge, LA 70813, USA, and ^bDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
^*Correspondence e-mail: ffroncz@lsu.edu

(Received 23 October 2008; accepted 29 October 2008; online 13 November 2008)

The title molecule, C₁₁H₁₃NO₃, has its propanoic acid group in an extended conformation, such that the molecule is nearly planar, with a mean deviation of 0.036 Å [the maxima being 0.106 (1) and 0.110 (1) Å for the two methylene C atoms]. The NH group forms an intramolecular hydrogen bond with the acetyl group; in the crystal COOH group forms a centrosymmetric hydrogen-bonded dimer.

Related literature

For general background, see: Crosby et al. (1961 , 1962 ); Foley et al. (2003 ); Walker Jr et al. (2004 ); Yoshihara et al. (2001 ). For related structures, see: Slater et al. (2006 ). For hydrogen-bonding patterns, see: Etter (1990 ).

Experimental

Crystal data

C₁₁H₁₃NO₃
M_r = 207.22
Triclinic, $[P \overline 1]$
a = 5.1935 (10) Å
b = 9.8342 (16) Å
c = 9.920 (2) Å
α = 77.084 (12)°
β = 85.174 (11)°
γ = 83.019 (12)°
V = 489.32 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 90.0 (5) K
0.30 × 0.20 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler
Absorption correction: none
11014 measured reflections
3012 independent reflections
2467 reflections with I > 2s(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.113
S = 1.04
3012 reflections
143 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O3ⁱ	0.909 (16)	1.747 (16)	2.6531 (11)	174.7 (14)
N1—H1N⋯O1	0.887 (14)	1.980 (14)	2.6690 (12)	133.4 (11)
Symmetry code: (i) -x, -y, -z+2.

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035277/pv2116sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035277/pv2116Isup2.hkl

checkCIF report

Comment top

Since the discovery that energy transfer from the triplet state of an organic ligand can efficiently sensitize the emissive states of metal ions (Crosby et al., 1961; 1962) there has been considerable effort devoted to designing ligands that optimize this energy transfer and thus give efficient metal luminescence (Foley et al., 2003). The radiationless energy transfer photoluminescence and/or electro-luminescence properties of aromatic carbonyl compounds are strongly affected by the presence of a substituent on the aromatic ring. In general, the π, π^* state is stabilized by introducing an electron-donating substituent on the aromatic ring, while the location of the n, π^* state is only slightly modified by the electron-donating substituent. Thus, the fluorescence properties of the compounds with close-lying ¹(n, π^*) and ¹(π, π^*) states are expected to depend markedly on the nature of the solvent, such as its polarity and hydrogen-bonding ability. In 2'-aminoacetophenone, the ¹(n, π^*) and ¹(π, π^*) states are closely located in the lowest excited singlet state because of the presence of a strong electron-donating substituent. Owing to the proximity of two electronic levels, the photophysical properties of 2'-aminoacetophenone is very sensitive to environment, such as solvent polarity and temperature (Yoshihara et al., 2001). Therefore, the addition of a strong electron-donating substituent such as acrylic acid, which has the ability to form a solventless gel via hydrogen bonding, has been synthesized. The structure of the title compound, also known as 3-[(N-acetyl-phenyl)-azanediyl]-propionic acid, is herein described. Its synthesis takes advantage of the self-initiating condensation of 2'-aminoacetophenone with the vinyl group of the ab unsaturated acrylic acid via anti-Markovnikov addition, which is similar to chemistry involved in the synthesis of the novel 3,3',3"-nitrilotripropionic acid precursor gel that we have developed (Walker, et al., 2004).

The structure of the molecule is shown in Figure 1. The acetyl group is nearly coplanar with the phenyl group, the C2—C1—C7—O2 torsion angle being -1.64 (15)°. The NH(CH₂)₂COOH substituent is extended, with torsion angles C1—C2—N1—C9 - 176.52 (9), C2—N1—C9—C10 - 172.10 (9), N1—C9—C10—C11 179.81 (8), and C9—C10—C11—O2 173.73 (8)°. Thus, the molecule does not differ greatly from planarity, with mean and maximum deviations given in the abstract. The geometry of the intramolecular hydrogen bond, graph set S(6), (Etter, 1990) is given in Table 1, and is quite similar to that found in N-(2-acetylphenyl)acetamide (Slater et al., 2006). The COOH group forms a typical hydrogen bonded dimer of graph set R²₂(8) about an inversion center, thus there are no extended networks of traditional hydrogen bonds.

Related literature top

For general background, see: Crosby et al. (1961, 1962); Foley et al. (2003); Walker Jr et al. (2004); Yoshihara et al. (2001). For related structures, see: Slater et al. (2006). For hydrogen-bonding patterns, see: Etter (1990).

Experimental top

A round bottom flask containing acrylic acid (1.051 g, 14.58 mmol) was stoppered and placed into the refrigerator overnight. In a similar round bottom flask, 2'-aminoacetophenoneHCl (1.0056 g, 0.79199 g of liberated 2-aminoacetophenone 5.861 mmol) was dissolved in 10 ml of deionized water and chilled overnight. The round bottom flask containing the cold acrylic acid was then placed into to an ice bath to maintain a temperature of approximately 273 K. The ice bath was used because the reaction of acrylic acid and 2'-aminoacetophenone was thought to be exothermic. The cold 2'-aminoacetophenone solution was slowly added with stirring to the cold acrylic acid. The mixture was allowed to sit in the ice bath for 30 minutes and then gradually warmed to room temperature, then kept at room temperature with continuous stirring overnight. A yellow precipitate was isolated by gravimetric filtration and washed with deionized water. The yellow solid material resulted in a yield of 0.8963 g (79.991%).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the title compound; ellipsoids have been plotted at the 50% level and H atoms have been assigned arbitrary radii.

3-(2-Acetylanilino)propanoic acid top

Crystal data top

C₁₁H₁₃NO₃	Z = 2
M_r = 207.22	F(000) = 220
Triclinic, P1	D_x = 1.406 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.1935 (10) Å	Cell parameters from 2652 reflections
b = 9.8342 (16) Å	θ = 2.5–30.8°
c = 9.920 (2) Å	µ = 0.10 mm⁻¹
α = 77.084 (12)°	T = 90 K
β = 85.174 (11)°	Fragment, colorless
γ = 83.019 (12)°	0.30 × 0.20 × 0.10 mm
V = 489.32 (16) Å³

Data collection top

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler	2467 reflections with I > 2s(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 30.8°, θ_min = 2.6°
ω scans with κ offsets	h = −7→7
11014 measured reflections	k = −13→13
3012 independent reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0573P)² + 0.1339P] where P = (F_o² + 2F_c²)/3
3012 reflections	(Δ/σ)_max < 0.001
143 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₁H₁₃NO₃	γ = 83.019 (12)°
M_r = 207.22	V = 489.32 (16) Å³
Triclinic, P1	Z = 2
a = 5.1935 (10) Å	Mo Kα radiation
b = 9.8342 (16) Å	µ = 0.10 mm⁻¹
c = 9.920 (2) Å	T = 90 K
α = 77.084 (12)°	0.30 × 0.20 × 0.10 mm
β = 85.174 (11)°

Data collection top

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler	2467 reflections with I > 2s(I)
11014 measured reflections	R_int = 0.021
3012 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.39 e Å⁻³
3012 reflections	Δρ_min = −0.29 e Å⁻³
143 parameters

Special details top

Experimental. ¹H (CDCl₃): δ(p.p.m.) 9.02 (s, 1H), 7.78 (d, J = 8.0 Hz, 1H), 7.38 (t, J = 8.0 Hz, 1H), 6.74 (d, J = 8.0 Hz, 1H), 6.62 (t, J = 8.0 Hz, 1H), 3.58 (t, J = 7.0 Hz, 2H), 2.73 (t, J = 7.0 Hz, 2H), and 2.60 (s, 3H). ¹³C (CDCl₃): δ (p.p.m.) 201.1, 176.7, 150.5, 135.2, 132.9, 117.9, 114.5, 111.3, 37.9, 33.8, and 27.9. IR (thin film, KBr plates, cm^-1): 3297 (m), 2925 (w, br), 2881 (sh, w), 2635 (w), 2373 (w), 1698 (s), 1634 (s), 1569 (m), 1517 (m), 1430 (m), 1366 (sh), 1326(m), 1240 (s), 1156 (w), 1092(w), 1031(w), 943 (m), 825(w), 742 (m), 675(w), and 624 (w). Crystals were grown by evaporation from CDCl₃.

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

	x	y	z	U_iso*/U_eq
O1	0.96261 (15)	0.13504 (8)	0.35274 (7)	0.01656 (17)
O2	0.30686 (15)	−0.07587 (8)	0.93327 (7)	0.01593 (17)
H2O	0.183 (3)	−0.0849 (15)	1.0039 (16)	0.024*
O3	0.04143 (14)	0.11745 (8)	0.85415 (7)	0.01599 (17)
N1	0.53905 (17)	0.21868 (9)	0.49711 (8)	0.01437 (18)
H1N	0.673 (3)	0.1541 (14)	0.4924 (13)	0.017*
C1	0.70722 (18)	0.35189 (10)	0.27655 (10)	0.01194 (19)
C2	0.51897 (19)	0.33391 (10)	0.39115 (10)	0.01242 (19)
C3	0.3083 (2)	0.43948 (11)	0.39170 (10)	0.0161 (2)
H3	0.1787	0.4282	0.4657	0.019*
C4	0.2866 (2)	0.55873 (11)	0.28701 (11)	0.0168 (2)
H4	0.1438	0.6283	0.2906	0.020*
C5	0.4725 (2)	0.57819 (11)	0.17590 (11)	0.0165 (2)
H5	0.4581	0.6605	0.1043	0.020*
C6	0.6778 (2)	0.47510 (10)	0.17238 (10)	0.0145 (2)
H6	0.8038	0.4879	0.0967	0.017*
C7	0.92650 (19)	0.24478 (10)	0.26361 (10)	0.01281 (19)
C8	1.1133 (2)	0.26868 (11)	0.13707 (10)	0.0157 (2)
H8A	1.2116	0.3472	0.1386	0.024*
H8B	1.0155	0.2905	0.0532	0.024*
H8C	1.2337	0.1838	0.1374	0.024*
C9	0.34277 (19)	0.19459 (11)	0.61054 (10)	0.0142 (2)
H9A	0.1798	0.1767	0.5757	0.017*
H9B	0.3060	0.2789	0.6508	0.017*
C10	0.43852 (19)	0.06928 (10)	0.72115 (10)	0.01378 (19)
H10A	0.4756	−0.0145	0.6801	0.017*
H10B	0.6025	0.0875	0.7548	0.017*
C11	0.24229 (19)	0.04048 (10)	0.84099 (10)	0.01244 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0166 (4)	0.0146 (3)	0.0149 (3)	0.0019 (3)	0.0026 (3)	0.0012 (3)
O2	0.0148 (4)	0.0162 (4)	0.0127 (3)	0.0014 (3)	0.0038 (3)	0.0020 (3)
O3	0.0152 (4)	0.0162 (4)	0.0132 (3)	0.0019 (3)	0.0041 (3)	0.0003 (3)
N1	0.0136 (4)	0.0144 (4)	0.0111 (4)	0.0025 (3)	0.0048 (3)	0.0014 (3)
C1	0.0110 (4)	0.0123 (4)	0.0114 (4)	−0.0009 (3)	0.0016 (3)	−0.0012 (3)
C2	0.0127 (4)	0.0134 (4)	0.0104 (4)	−0.0015 (3)	0.0016 (3)	−0.0018 (3)
C3	0.0145 (5)	0.0179 (5)	0.0141 (4)	0.0014 (4)	0.0030 (3)	−0.0027 (4)
C4	0.0160 (5)	0.0150 (5)	0.0177 (5)	0.0030 (4)	0.0004 (4)	−0.0030 (4)
C5	0.0174 (5)	0.0135 (4)	0.0162 (5)	0.0002 (4)	0.0000 (4)	0.0005 (3)
C6	0.0152 (4)	0.0145 (4)	0.0125 (4)	−0.0021 (4)	0.0021 (3)	−0.0006 (3)
C7	0.0115 (4)	0.0146 (4)	0.0118 (4)	−0.0016 (3)	0.0015 (3)	−0.0024 (3)
C8	0.0146 (4)	0.0162 (5)	0.0136 (4)	0.0001 (4)	0.0045 (3)	−0.0005 (3)
C9	0.0126 (4)	0.0169 (5)	0.0109 (4)	−0.0001 (3)	0.0033 (3)	−0.0008 (3)
C10	0.0126 (4)	0.0155 (4)	0.0113 (4)	−0.0007 (3)	0.0028 (3)	−0.0005 (3)
C11	0.0132 (4)	0.0130 (4)	0.0107 (4)	−0.0022 (3)	0.0015 (3)	−0.0020 (3)

Geometric parameters (Å, º) top

O1—C7	1.2384 (12)	C4—H4	0.9500
O2—C11	1.3228 (12)	C5—C6	1.3829 (14)
O2—H2O	0.909 (16)	C5—H5	0.9500
O3—C11	1.2278 (12)	C6—H6	0.9500
N1—C2	1.3628 (12)	C7—C8	1.5135 (13)
N1—C9	1.4519 (12)	C8—H8A	0.9800
N1—H1N	0.887 (14)	C8—H8B	0.9800
C1—C6	1.4075 (13)	C8—H8C	0.9800
C1—C2	1.4299 (13)	C9—C10	1.5193 (14)
C1—C7	1.4722 (14)	C9—H9A	0.9900
C2—C3	1.4145 (14)	C9—H9B	0.9900
C3—C4	1.3819 (14)	C10—C11	1.4993 (13)
C3—H3	0.9500	C10—H10A	0.9900
C4—C5	1.3983 (15)	C10—H10B	0.9900

C11—O2—H2O	108.7 (9)	O1—C7—C8	118.76 (9)
C2—N1—C9	122.44 (8)	C1—C7—C8	119.13 (8)
C2—N1—H1N	117.8 (9)	C7—C8—H8A	109.5
C9—N1—H1N	119.7 (9)	C7—C8—H8B	109.5
C6—C1—C2	118.53 (9)	H8A—C8—H8B	109.5
C6—C1—C7	119.47 (9)	C7—C8—H8C	109.5
C2—C1—C7	122.00 (8)	H8A—C8—H8C	109.5
N1—C2—C3	120.39 (9)	H8B—C8—H8C	109.5
N1—C2—C1	121.56 (9)	N1—C9—C10	109.68 (8)
C3—C2—C1	118.05 (9)	N1—C9—H9A	109.7
C4—C3—C2	121.48 (9)	C10—C9—H9A	109.7
C4—C3—H3	119.3	N1—C9—H9B	109.7
C2—C3—H3	119.3	C10—C9—H9B	109.7
C3—C4—C5	120.76 (9)	H9A—C9—H9B	108.2
C3—C4—H4	119.6	C11—C10—C9	111.66 (8)
C5—C4—H4	119.6	C11—C10—H10A	109.3
C6—C5—C4	118.62 (9)	C9—C10—H10A	109.3
C6—C5—H5	120.7	C11—C10—H10B	109.3
C4—C5—H5	120.7	C9—C10—H10B	109.3
C5—C6—C1	122.54 (9)	H10A—C10—H10B	107.9
C5—C6—H6	118.7	O3—C11—O2	122.63 (9)
C1—C6—H6	118.7	O3—C11—C10	123.78 (9)
O1—C7—C1	122.11 (9)	O2—C11—C10	113.59 (8)

C9—N1—C2—C3	3.20 (15)	C2—C1—C6—C5	−0.84 (15)
C9—N1—C2—C1	−176.52 (9)	C7—C1—C6—C5	178.13 (10)
C6—C1—C2—N1	−178.48 (9)	C6—C1—C7—O1	179.42 (9)
C7—C1—C2—N1	2.57 (15)	C2—C1—C7—O1	−1.64 (15)
C6—C1—C2—C3	1.80 (14)	C6—C1—C7—C8	−0.98 (14)
C7—C1—C2—C3	−177.15 (9)	C2—C1—C7—C8	177.96 (9)
N1—C2—C3—C4	178.57 (10)	C2—N1—C9—C10	−172.10 (9)
C1—C2—C3—C4	−1.71 (15)	N1—C9—C10—C11	179.81 (8)
C2—C3—C4—C5	0.58 (16)	C9—C10—C11—O3	−6.99 (14)
C3—C4—C5—C6	0.45 (16)	C9—C10—C11—O2	173.73 (8)
C4—C5—C6—C1	−0.30 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3ⁱ	0.909 (16)	1.747 (16)	2.6531 (11)	174.7 (14)
N1—H1N···O1	0.887 (14)	1.980 (14)	2.6690 (12)	133.4 (11)

Symmetry code: (i) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃NO₃
M_r	207.22
Crystal system, space group	Triclinic, P1
Temperature (K)	90
a, b, c (Å)	5.1935 (10), 9.8342 (16), 9.920 (2)
α, β, γ (°)	77.084 (12), 85.174 (11), 83.019 (12)
V (Å³)	489.32 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler
Absorption correction	–
No. of measured, independent and observed [I > 2s(I)] reflections	11014, 3012, 2467
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.720

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.113, 1.04
No. of reflections	3012
No. of parameters	143
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.29

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3ⁱ	0.909 (16)	1.747 (16)	2.6531 (11)	174.7 (14)
N1—H1N···O1	0.887 (14)	1.980 (14)	2.6690 (12)	133.4 (11)

Symmetry code: (i) −x, −y, −z+2.

Acknowledgements

This research was made possible by a grant supplied by the National Science Foundation's Early CAREER program (Cooperative Agreement DMR-0449886) at Southern University, and by a grant supplied by the US Deptartment of Education Title III Part B HBGI program (grant No. P031B040030) at Southern University. The purchase of the NMR was made possible by the National Science Foundation's Major Research Instrument Program (Cooperative Agreement CHE-0321591) at Southern University. The purchase of the FTIR was made possible by grant No. LEQSF(2005–2007)-ENH-TR-65, and the purchase of the diffractometer was made possible by grant No. LEQSF (1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents.

References

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Volume 64| Part 12| December 2008| Page o2359

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