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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

4-{(E)-N′-[2-(8-Quinolyl­oxy)acetyl]hydrazono­methyl}benzoic acid methanol solvate

aCollege of Chemistry and Pharmacy, Qingdao Agricultural University, Shandong 266109, People's Republic of China
*Correspondence e-mail: furbear01@163.com

(Received 2 April 2009; accepted 6 June 2009; online 17 June 2009)

In the title compound, C19H15N3O4·CH4O, the mean planes of the benzene ring and the quinoline system make a dihedral angle of 6.7 (2)°. The acetohydrazide host mol­ecules are connected via inter­molecular O—H⋯O hydrogen bonds into two-dimensional zigzag sheets extending in the ab plane. The methanol solvent mol­ecule is linked to the host mol­ecule via inter­molecular N—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For the coordination chemistry of 8-hydroxy­quinoline and its derivatives, see: Chen & Shi (1998[Chen, C. H. & Shi, J. M. (1998). Coord. Chem. Rev. 171, 161—174.]). For a related structure, see: Wen et al. (2005[Wen, Y.-H., Zhang, S.-S., Li, M.-J. & Li, X.-M. (2005). Acta Cryst. E61, o2045-o2046.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C19H15N3O4·CH4O

  • Mr = 381.38

  • Monoclinic, P 21 /c

  • a = 10.1166 (18) Å

  • b = 11.095 (2) Å

  • c = 18.510 (3) Å

  • β = 115.896 (7)°

  • V = 1869.0 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 295 K

  • 0.22 × 0.19 × 0.18 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.979, Tmax = 0.982

  • 9663 measured reflections

  • 3302 independent reflections

  • 1666 reflections with I > 2σ(I)

  • Rint = 0.046

Refinement
  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.161

  • S = 1.02

  • 3302 reflections

  • 255 parameters

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3⋯O2i 0.82 1.88 2.695 (3) 171
O5—H5⋯N1 0.82 1.95 2.765 (3) 171
N2—H2⋯O5 0.86 2.01 2.838 (4) 162
Symmetry code: (i) [-x+3, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments 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

8-Hydroxyquinoline and its derivatives constitute well known ligands in coordination chemistry (Chen & Shi, 1998). As part of our on going search for good extractants of metal ions or a biologically active material, the title compound was obtained in the reaction of quinolin-8-yloxyacetic acid hydrazide and 4-formylbenzoic acid. In the crystal structure of all bond lengths and angles are normal (Allen et al., 1987), and are comparable to those in the related compound N'-(2-Fluorobenzylidene)-2-(quinolin-8-yloxy)-acetohydrazide methanol solvate (Wen et al., 2005). The mean planes of the benzene ring and the quinoline ring make a dihedral angle of 6.7 (2)°. In the crystal structure, the methanol molecule is linked to the C19H15N3O4 host molecule via intermolecular N—H···O and O—H···N hydrogen bonds (Fig. 1). Intermolecular O—H···O hydrogen bonds (Table 1) fuse the molecules into two-dimensional zig-zag sheets along the a*-b* plane (Fig. 2).

Related literature top

For the coordination chemistry of 8-hydroxyquinoline and its derivatives, see: Chen & Shi (1998). For a related structure, see: Wen et al. (2005). For bond-length data, see: Allen et al. (1987).

Experimental top

2-(quinolin-8-yloxy)acetohydrazide (2.18 g, 10 mmol), 4-formylbenzoic acid (1.50 g, 10 mmol), ethanol (40 ml) and some drops of acetic acid were added to a 100 ml flask, and refluxed for 3 h. After cooling to room temperature, the mixture was filtered. Colourless single crystals suitable for X-ray diffraction study were obtained by slow evaporation of a acetone-methanol (1:2, v/v) solution over a period of 2 d.

Refinement top

All H atoms were initially located in a difference Fourier map. C-atoms bound H atoms were constrained to ideal geometry with C—H = 0.93 Å for aryl, 0.97 Å for the methylene, and 0.96 Å for the methyl H atoms, while O—H = 0.82 Å and N—H = 0.86 Å were applied. H-atoms displacement values were constarined as Uiso(H) = 1.2Ueq(C,N), or 1.5Ueq(C) for the methyl groups, and 1.5Ueq(O).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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. The asymmetric unit structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. The dashed lines indicate hydrogen bonds.
[Figure 2] Fig. 2. The H-bonding sheet from the crystal structure supported via hydrogen bridges (dashed lines), with only relevant H atoms shown for clarity.
4-{(E)-N'-[2-(8-Quinolyloxy)acetyl]hydrazonomethyl}benzoic acid methanol solvate top
Crystal data top
C19H15N3O4·CH4OF(000) = 800
Mr = 381.38Dx = 1.355 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1033 reflections
a = 10.1166 (18) Åθ = 2.9–20.4°
b = 11.095 (2) ŵ = 0.10 mm1
c = 18.510 (3) ÅT = 295 K
β = 115.896 (7)°Block, colorless
V = 1869.0 (6) Å30.22 × 0.19 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3302 independent reflections
Radiation source: fine-focus sealed tube1666 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
ϕ and ω scansθmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 912
Tmin = 0.979, Tmax = 0.982k = 1311
9663 measured reflectionsl = 2215
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0693P)2 + 0.0146P]
where P = (Fo2 + 2Fc2)/3
3302 reflections(Δ/σ)max < 0.001
255 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C19H15N3O4·CH4OV = 1869.0 (6) Å3
Mr = 381.38Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.1166 (18) ŵ = 0.10 mm1
b = 11.095 (2) ÅT = 295 K
c = 18.510 (3) Å0.22 × 0.19 × 0.18 mm
β = 115.896 (7)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3302 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1666 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.982Rint = 0.046
9663 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.161H-atom parameters constrained
S = 1.02Δρmax = 0.20 e Å3
3302 reflectionsΔρmin = 0.20 e Å3
255 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.63801 (19)0.10228 (18)0.61156 (11)0.0599 (6)
O20.9689 (2)0.0368 (2)0.74781 (14)0.0785 (7)
O31.7457 (2)0.4174 (2)0.71168 (15)0.0813 (7)
H31.83460.42740.72840.122*
O41.8166 (2)0.2717 (2)0.80207 (16)0.1010 (9)
O50.7722 (3)0.3037 (3)0.55054 (17)0.1139 (11)
H50.68570.28430.53430.171*
N10.4754 (3)0.2645 (3)0.50135 (15)0.0710 (8)
N20.9278 (2)0.1277 (2)0.66847 (14)0.0584 (7)
H20.86460.17620.63470.070*
N31.0764 (2)0.1439 (2)0.69304 (14)0.0571 (7)
C10.3936 (4)0.3439 (4)0.4474 (2)0.0946 (12)
H10.44140.40640.43510.113*
C20.2410 (4)0.3411 (4)0.4076 (2)0.1093 (14)
H2A0.18920.39980.37000.131*
C30.1702 (4)0.2509 (4)0.4249 (2)0.0895 (12)
H3A0.06820.24650.39880.107*
C40.2502 (3)0.1634 (3)0.48242 (18)0.0657 (9)
C50.1831 (4)0.0687 (4)0.5031 (2)0.0820 (11)
H5A0.08130.06120.47820.098*
C60.2653 (4)0.0124 (3)0.5593 (2)0.0830 (11)
H60.21920.07470.57320.100*
C70.4194 (3)0.0038 (3)0.5971 (2)0.0694 (9)
H70.47420.06040.63560.083*
C80.4887 (3)0.0864 (3)0.57778 (16)0.0542 (8)
C90.4050 (3)0.1729 (3)0.51962 (17)0.0563 (8)
C100.7231 (3)0.0167 (3)0.67118 (18)0.0582 (8)
H10A0.69630.06400.64950.070*
H10B0.70070.02380.71690.070*
C110.8852 (3)0.0348 (3)0.69869 (19)0.0569 (8)
C121.1136 (3)0.2365 (3)0.66626 (17)0.0616 (8)
H121.04180.28930.63240.074*
C131.2683 (3)0.2610 (3)0.68819 (17)0.0553 (8)
C141.3077 (3)0.3561 (3)0.65354 (18)0.0634 (9)
H141.23510.40540.61680.076*
C151.4531 (3)0.3789 (3)0.67266 (17)0.0611 (8)
H151.47740.44260.64810.073*
C161.5624 (3)0.3087 (3)0.72761 (17)0.0529 (8)
C171.5237 (3)0.2143 (3)0.76234 (19)0.0661 (9)
H171.59690.16600.79960.079*
C181.3783 (3)0.1893 (3)0.74314 (18)0.0634 (9)
H181.35440.12460.76710.076*
C191.7212 (3)0.3295 (3)0.7518 (2)0.0640 (9)
C200.7908 (5)0.3609 (5)0.4924 (3)0.158 (2)
H20A0.84340.43470.51300.236*
H20B0.69670.37860.44910.236*
H20C0.84590.31070.47310.236*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0316 (11)0.0766 (15)0.0663 (12)0.0052 (9)0.0166 (9)0.0076 (11)
O20.0439 (13)0.0783 (16)0.1085 (17)0.0127 (11)0.0290 (12)0.0269 (14)
O30.0437 (13)0.0831 (18)0.1124 (18)0.0145 (12)0.0296 (13)0.0009 (14)
O40.0376 (13)0.126 (2)0.120 (2)0.0027 (14)0.0169 (13)0.0300 (18)
O50.0558 (16)0.152 (3)0.114 (2)0.0054 (17)0.0187 (15)0.065 (2)
N10.0464 (16)0.096 (2)0.0650 (16)0.0006 (15)0.0193 (13)0.0115 (15)
N20.0301 (13)0.0731 (18)0.0675 (16)0.0000 (11)0.0173 (12)0.0058 (13)
N30.0347 (14)0.0673 (19)0.0693 (16)0.0030 (12)0.0226 (12)0.0025 (13)
C10.063 (3)0.113 (3)0.090 (3)0.002 (2)0.017 (2)0.034 (2)
C20.061 (3)0.146 (4)0.099 (3)0.015 (3)0.014 (2)0.035 (3)
C30.042 (2)0.130 (4)0.079 (2)0.001 (2)0.0101 (19)0.003 (2)
C40.0347 (17)0.097 (3)0.0587 (19)0.0039 (17)0.0137 (15)0.0129 (18)
C50.0358 (19)0.116 (3)0.086 (2)0.015 (2)0.0189 (18)0.018 (2)
C60.051 (2)0.097 (3)0.102 (3)0.026 (2)0.034 (2)0.012 (2)
C70.0426 (18)0.082 (2)0.082 (2)0.0115 (17)0.0262 (17)0.0001 (18)
C80.0351 (16)0.072 (2)0.0551 (18)0.0051 (15)0.0197 (14)0.0090 (15)
C90.0375 (17)0.078 (2)0.0539 (17)0.0065 (15)0.0199 (14)0.0074 (16)
C100.0399 (17)0.066 (2)0.0674 (19)0.0008 (15)0.0222 (15)0.0061 (16)
C110.0386 (17)0.063 (2)0.071 (2)0.0008 (15)0.0256 (16)0.0017 (17)
C120.0340 (17)0.074 (2)0.069 (2)0.0005 (15)0.0151 (15)0.0062 (17)
C130.0381 (17)0.062 (2)0.0602 (18)0.0018 (14)0.0167 (14)0.0031 (15)
C140.0411 (18)0.070 (2)0.069 (2)0.0000 (15)0.0145 (15)0.0123 (16)
C150.0451 (19)0.063 (2)0.070 (2)0.0090 (15)0.0208 (16)0.0031 (16)
C160.0358 (16)0.057 (2)0.0625 (18)0.0063 (14)0.0180 (14)0.0115 (15)
C170.0411 (18)0.073 (2)0.078 (2)0.0042 (16)0.0203 (16)0.0082 (18)
C180.0443 (18)0.067 (2)0.079 (2)0.0015 (15)0.0269 (16)0.0113 (17)
C190.044 (2)0.069 (2)0.076 (2)0.0083 (17)0.0242 (18)0.0094 (19)
C200.088 (4)0.201 (6)0.163 (5)0.004 (3)0.036 (3)0.073 (4)
Geometric parameters (Å, º) top
O1—C81.371 (3)C6—C71.406 (4)
O1—C101.425 (3)C6—H60.9300
O2—C111.225 (3)C7—C81.357 (4)
O3—C191.313 (4)C7—H70.9300
O3—H30.8200C8—C91.415 (4)
O4—C191.193 (4)C10—C111.503 (4)
O5—C201.332 (5)C10—H10A0.9700
O5—H50.8200C10—H10B0.9700
N1—C11.318 (4)C12—C131.461 (4)
N1—C91.365 (4)C12—H120.9300
N2—C111.332 (3)C13—C141.382 (4)
N2—N31.379 (3)C13—C181.384 (4)
N2—H20.8600C14—C151.378 (4)
N3—C121.267 (3)C14—H140.9300
C1—C21.390 (5)C15—C161.372 (4)
C1—H10.9300C15—H150.9300
C2—C31.348 (5)C16—C171.372 (4)
C2—H2A0.9300C16—C191.486 (4)
C3—C41.407 (5)C17—C181.381 (4)
C3—H3A0.9300C17—H170.9300
C4—C51.393 (5)C18—H180.9300
C4—C91.413 (4)C20—H20A0.9600
C5—C61.351 (5)C20—H20B0.9600
C5—H5A0.9300C20—H20C0.9600
C8—O1—C10116.1 (2)C11—C10—H10A109.2
C19—O3—H3109.5O1—C10—H10B109.2
C20—O5—H5109.5C11—C10—H10B109.2
C1—N1—C9117.5 (3)H10A—C10—H10B107.9
C11—N2—N3118.0 (2)O2—C11—N2124.6 (3)
C11—N2—H2121.0O2—C11—C10117.6 (3)
N3—N2—H2121.0N2—C11—C10117.8 (3)
C12—N3—N2116.3 (2)N3—C12—C13120.5 (3)
N1—C1—C2124.9 (4)N3—C12—H12119.8
N1—C1—H1117.6C13—C12—H12119.8
C2—C1—H1117.6C14—C13—C18118.5 (3)
C3—C2—C1118.2 (4)C14—C13—C12120.3 (3)
C3—C2—H2A120.9C18—C13—C12121.2 (3)
C1—C2—H2A120.9C15—C14—C13120.9 (3)
C2—C3—C4120.2 (3)C15—C14—H14119.6
C2—C3—H3A119.9C13—C14—H14119.6
C4—C3—H3A119.9C16—C15—C14120.7 (3)
C5—C4—C3122.7 (3)C16—C15—H15119.7
C5—C4—C9119.5 (3)C14—C15—H15119.7
C3—C4—C9117.8 (3)C15—C16—C17118.6 (3)
C6—C5—C4120.3 (3)C15—C16—C19123.4 (3)
C6—C5—H5A119.9C17—C16—C19118.0 (3)
C4—C5—H5A119.9C16—C17—C18121.4 (3)
C5—C6—C7120.9 (3)C16—C17—H17119.3
C5—C6—H6119.5C18—C17—H17119.3
C7—C6—H6119.5C17—C18—C13119.9 (3)
C8—C7—C6120.5 (3)C17—C18—H18120.1
C8—C7—H7119.8C13—C18—H18120.1
C6—C7—H7119.8O4—C19—O3123.5 (3)
C7—C8—O1124.6 (3)O4—C19—C16123.4 (3)
C7—C8—C9119.7 (3)O3—C19—C16113.1 (3)
O1—C8—C9115.7 (3)O5—C20—H20A109.5
N1—C9—C4121.5 (3)O5—C20—H20B109.5
N1—C9—C8119.3 (3)H20A—C20—H20B109.5
C4—C9—C8119.2 (3)O5—C20—H20C109.5
O1—C10—C11112.0 (2)H20A—C20—H20C109.5
O1—C10—H10A109.2H20B—C20—H20C109.5
C11—N2—N3—C12176.6 (3)O1—C8—C9—C4179.5 (2)
C9—N1—C1—C20.2 (6)C8—O1—C10—C11174.5 (2)
N1—C1—C2—C30.0 (7)N3—N2—C11—O21.1 (5)
C1—C2—C3—C40.5 (6)N3—N2—C11—C10179.4 (2)
C2—C3—C4—C5179.6 (4)O1—C10—C11—O2177.3 (3)
C2—C3—C4—C90.9 (6)O1—C10—C11—N23.1 (4)
C3—C4—C5—C6179.5 (3)N2—N3—C12—C13179.4 (2)
C9—C4—C5—C61.1 (5)N3—C12—C13—C14174.4 (3)
C4—C5—C6—C70.8 (5)N3—C12—C13—C184.9 (5)
C5—C6—C7—C80.0 (5)C18—C13—C14—C150.5 (5)
C6—C7—C8—O1179.7 (3)C12—C13—C14—C15178.9 (3)
C6—C7—C8—C90.5 (5)C13—C14—C15—C161.0 (5)
C10—O1—C8—C70.3 (4)C14—C15—C16—C170.8 (4)
C10—O1—C8—C9179.0 (2)C14—C15—C16—C19179.0 (3)
C1—N1—C9—C40.1 (5)C15—C16—C17—C180.1 (5)
C1—N1—C9—C8179.4 (3)C19—C16—C17—C18179.8 (3)
C5—C4—C9—N1179.8 (3)C16—C17—C18—C130.5 (5)
C3—C4—C9—N10.7 (5)C14—C13—C18—C170.3 (5)
C5—C4—C9—C80.5 (4)C12—C13—C18—C17179.6 (3)
C3—C4—C9—C8180.0 (3)C15—C16—C19—O4176.7 (3)
C7—C8—C9—N1179.1 (3)C17—C16—C19—O43.2 (5)
O1—C8—C9—N10.3 (4)C15—C16—C19—O33.9 (4)
C7—C8—C9—C40.2 (4)C17—C16—C19—O3176.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.821.882.695 (3)171
O5—H5···N10.821.952.765 (3)171
N2—H2···O50.862.012.838 (4)162
Symmetry code: (i) x+3, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC19H15N3O4·CH4O
Mr381.38
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)10.1166 (18), 11.095 (2), 18.510 (3)
β (°) 115.896 (7)
V3)1869.0 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.22 × 0.19 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.979, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
9663, 3302, 1666
Rint0.046
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.161, 1.02
No. of reflections3302
No. of parameters255
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.20

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.821.882.695 (3)171.3
O5—H5···N10.821.952.765 (3)170.6
N2—H2···O50.862.012.838 (4)162.0
Symmetry code: (i) x+3, y+1/2, z+3/2.
 

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationChen, C. H. & Shi, J. M. (1998). Coord. Chem. Rev. 171, 161—174.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
First citationWen, Y.-H., Zhang, S.-S., Li, M.-J. & Li, X.-M. (2005). Acta Cryst. E61, o2045–o2046.  Web of Science CSD CrossRef IUCr Journals 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
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds