The title compound has an E conformation with respect to the azomethine C=N bond and the aromatic rings are inclined to one another by 3.29 (4)°. In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming zigzag chains along [10-1].
Keywords: crystal structure, azastilbene, antibacterial, anti-oxidant, hydrogen bonding
Abstract
The title azastilbene derivative, C14H13NO2 {systematic name: (E)-2-[(4-methoxybenzylidene)amino]phenol}, is a product of the condensation reaction between 4-methoxybenzaldehyde and 2-aminophenol. The molecule adopts an E conformation with respect to the azomethine C=N bond and is almost planar, the dihedral angle between the two substituted benzene rings being 3.29 (4)°. The methoxy group is coplanar with the benzene ring to which it is attached, the Cmethyl—O—C—C torsion angle being −1.14 (12)°. There is an intramolecular O—H⋯N hydrogen bond generating an S(5) ring motif. In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming zigzag chains along [10-1]. The chains are linked via C—H⋯π interactions, forming a three-dimensional structure.
Chemical context
Azastilbenes have been reported to possess various biological activities such as antibacterial (Tamizh et al., 2012 ▸), anti-oxidant (Cheng et al., 2010 ▸; Lu et al., 2012 ▸), antifungal (da Silva et al., 2011 ▸) and antiproliferative (Fujita et al., 2012 ▸) including lipoxygenase inhibitor (Aslam et al., 2012b
▸) activities. PdII and RuIII complexes of azastilbenes have been synthesized and some have shown potent antibacterial activity (Briel et al., 1998 ▸; Prabhakaran et al., 2008 ▸; Puthilibai et al., 2009 ▸). The interesting biological activities of azastilbenes have attracted us to synthesis a series of azastilbenes, including the title compound, and to study their antibacterial and anti-oxidant activities (Kaewmanee et al., 2013 ▸, 2014 ▸). The antibacterial assay for the title compound indicated that it possesses moderate to weak antibacterial activity against B. subtilis, S. aureus, P. aeruginosa, S. typhi and S. sonnei with the MIC values in the range of 37.5 to 150 µg/ml. In addition, it also shows interesting antioxidant activity by DPPH assay with the IC50 value of 0.080±0.0004 µg/ml. Herein, we report on the synthesis, spectroscopic and crystallographic characterization of the title compound.
Structural commentary
The title azastilbene compound (Fig. 1 ▸) has an E conformation about the azomethine C7=N1 double bond [1.2825 (10) Å], the C8—N1—C7—C1 torsion angle being −178.67 (8)°. The molecule is almost planar with a dihedral angle of 3.29 (4)° between the two substituted benzene rings. The methoxy group is co-planar with the benzene ring to which it is attached, the C14—O1—C4—C5 torsion angle being −1.14 (12)°. There is an intramolecular O—H⋯N hydrogen bond (Fig. 1 ▸ and Table 1 ▸) that generates an S(5) ring motif. The bond lengths are comparable with those found for some closely related structures (Habibi et al., 2013 ▸; Aslam et al., 2012a ▸; Kaewmanee et al., 2013 ▸, 2014 ▸; Sun et al., 2011 ▸).
Figure 1.
The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 60% probability level. The intramolecular O—H⋯N hydrogen bond is shown as a dashed line (see Table 1 ▸).
Table 1. Hydrogen-bond geometry (, ).
Cg1 and Cg2 are the centroids of rings C1C6 and C8C13, respectively.
| DHA | DH | HA | D A | DHA |
|---|---|---|---|---|
| O2H1O2N1 | 0.774(18) | 2.078(17) | 2.6315(11) | 128.7(17) |
| C14H14BO2i | 0.96 | 2.71 | 3.2876(12) | 119 |
| C2H2A Cg2ii | 0.93 | 2.93 | 3.5662(9) | 127 |
| C13H13A Cg1iii | 0.93 | 2.76 | 3.4671(9) | 134 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
.
Supramolecular features
In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming zigzag chains along [10
] (Fig. 2 ▸ and Table 1 ▸). The chains are linked via C—H⋯π interactions (Fig. 3 ▸ and Table 1 ▸), forming a three-dimensional structure.
Figure 2.
A view along the b axis of the crystal packing of the title compound. The C—H⋯O hydrogen bonds are shown as dashed lines (see Table 1 ▸ for details).
Figure 3.
A view of the C—H⋯π interactions (dashed lines) in the crystal of the title compound (see Table 1 ▸ for details; ring centroids are shown as coloured spheres).
Database survey
A search of the Cambridge Structural Database (CSD, Version 5.36; Groom & Allen, 2014 ▸) for azastilbenes gave over 2800 hits. A search for 2-(benzylideneamino)phenols gave 78 hits, and for 2-[(4-methoxybenzylidene)amino]phenols there were five hits. In the compound that most closely resembles the title compound, namely 5-{[(2-hydroxyphenyl)imino]methyl}-2-methoxyphenol (Habibi et al., 2013 ▸), the two aromatic rings are inclined to one another by ca 16.9°.
Synthesis and crystallization
A solution of 4-methoxybenzaldehyde (2.5 mmol, 0.37 g) in water (20 ml) and 2-aminophenol (2.5 mmol, 0.25 g) in water (20 ml) were mixed and stirred at room temperature for around 8 h until a white precipitate appeared. The resulting white solid was filtered, washed several times with cold ethanol and then dried in vacuo overnight to yield the desired azastilbene (430 mg, 76% yield). Colourless block-shaped crystals, suitable for X-ray structure analysis, were obtained by recrystallization from methanol by slow evaporation at room temperature after several days (m.p. 388–390 K).
UV–Vis (CH3OH) λmax (log∊): 275 (1.93), 340 (0.61) nm; FT–IR (KBr) ν: 3337, 1595, 1510, 1248, 1027 cm−1.; 1H NMR (300 MHz, DMSO-d 6) δ, p.p.m.: 8.87 (s, 1H), 8.61 (s, 1H), 7.98 (d, J = 8.7 Hz, 2H), 7.18 (dd, J = 7.5, 1.2 Hz, 1H), 7.06 (d, J = 8.7 Hz, 2H), 7.03 (td, J = 7.5, 1.2 Hz, 1H), 6.83 (td, J = 7.5, 1.2 Hz, 1H), 6.09 (dd, J = 7.5, 1.2 Hz, 1H), 3.84 (s, –OCH3). The UV–Vis spectroscopic data showed absorption bands of an azastilbene (275 and 340 nm) while the FT–IR spectrum exhibited the stretching vibrations of O—H (3337 cm−1), C=N (1595 cm−1), C=C (1510 cm−1), C—N (1248 cm−1) and C—O (1027 cm−1). The successful synthesis was also supported by the 1H NMR spectroscopic data, which showed the characteristic signals of an olefinic proton at 8.61 (s, 1H) and para-substituted aromatic protons at 7.98 (d, J = 8.7 Hz, 2H) and 7.06 (d, J = 8.7 Hz, 2H), respectively. Moreover the 1H NMR spectrum also showed typical signals of ortho-substituted aromatic protons at 7.18 (dd, J = 7.5, 1.2 Hz, 1H), 7.03 (td, J = 7.5, 1.2 Hz, 1H), 6.83 (td, J = 7.5, 1.2 Hz, 1H) and 6.09 (dd, J = 7.5, 1.2 Hz, 1H) and a methoxy proton at 3.84 (s, –OCH3).
The antibacterial activity investigation of the title compound against Gram-positive bacteria, which are B. subtilis, S. aureus, MRSA and E. faecalis, and Gram-negative bacteria, which are P. aeruginosa, S. sonnei and S. typhi, showed moderate, mild or no inhibition. The most interesting antibacterial activity showed moderate activity against P. aeruginosa with an MIC value of 37.5 µg/ml.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The OH H atom was located in a difference Fourier map and freely refined. The C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms: C—H = 0.93–0.96 Å with U iso(H) = 1.5U eq(C) for methyl H atoms and 1.2U eq(C) for other H atoms.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C14H13NO2 |
| M r | 227.25 |
| Crystal system, space group | Monoclinic, P c |
| Temperature (K) | 100 |
| a, b, c () | 8.0357(3), 5.5554(2), 12.8733(5) |
| () | 101.312(1) |
| V (3) | 563.52(4) |
| Z | 2 |
| Radiation type | Mo K |
| (mm1) | 0.09 |
| Crystal size (mm) | 0.55 0.48 0.41 |
| Data collection | |
| Diffractometer | Bruker APEXII D8 Venture |
| Absorption correction | Multi-scan (SADABS; Bruker, 2009 ▸) |
| T min, T max | 0.953, 0.964 |
| No. of measured, independent and observed [I > 2(I)] reflections | 26314, 3449, 3414 |
| R int | 0.023 |
| (sin /)max (1) | 0.715 |
| Refinement | |
| R[F 2 > 2(F 2)], wR(F 2), S | 0.037, 0.100, 1.09 |
| No. of reflections | 3449 |
| No. of parameters | 160 |
| No. of restraints | 2 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| max, min (e 3) | 0.37, 0.28 |
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015008348/su5124sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015008348/su5124Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015008348/su5124Isup3.cml
CCDC reference: 1062128
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank the Department of Chemistry, Faculty of Science, Prince of Songkla University, for research facilities. The authors extend their appreciation to The Deanship of Scientific Research at King Saud University for funding this work through research group project No. RGP-VPP-207.
supplementary crystallographic information
Crystal data
| C14H13NO2 | Dx = 1.339 Mg m−3 |
| Mr = 227.25 | Melting point = 388–390 K |
| Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.0357 (3) Å | Cell parameters from 3449 reflections |
| b = 5.5554 (2) Å | θ = 2.6–30.5° |
| c = 12.8733 (5) Å | µ = 0.09 mm−1 |
| β = 101.312 (1)° | T = 100 K |
| V = 563.52 (4) Å3 | Block, colorless |
| Z = 2 | 0.55 × 0.48 × 0.41 mm |
| F(000) = 240 |
Data collection
| Bruker APEXII D8 Venture diffractometer | 3414 reflections with I > 2σ(I) |
| φ and ω scans | Rint = 0.023 |
| Absorption correction: multi-scan (SADABS; Bruker, 2009) | θmax = 30.5°, θmin = 2.6° |
| Tmin = 0.953, Tmax = 0.964 | h = −11→11 |
| 26314 measured reflections | k = −7→7 |
| 3449 independent reflections | l = −18→18 |
Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0786P)2 + 0.0298P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.09 | (Δ/σ)max < 0.001 |
| 3449 reflections | Δρmax = 0.37 e Å−3 |
| 160 parameters | Δρmin = −0.28 e Å−3 |
| 2 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.054 (8) |
Special details
| Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.29289 (8) | 0.08802 (12) | 0.07528 (5) | 0.01815 (14) | |
| O2 | 0.92146 (10) | 0.70962 (12) | 0.58775 (6) | 0.02323 (15) | |
| H1O2 | 0.859 (2) | 0.653 (3) | 0.5407 (15) | 0.028 (3)* | |
| N1 | 0.72131 (9) | 0.33548 (14) | 0.53665 (5) | 0.01630 (16) | |
| C1 | 0.54115 (10) | 0.13926 (16) | 0.38967 (6) | 0.01455 (16) | |
| C2 | 0.55623 (10) | 0.31817 (15) | 0.31478 (7) | 0.01598 (16) | |
| H2A | 0.6239 | 0.4524 | 0.3353 | 0.019* | |
| C3 | 0.47132 (10) | 0.29620 (15) | 0.21094 (7) | 0.01586 (16) | |
| H3A | 0.4826 | 0.4149 | 0.1618 | 0.019* | |
| C4 | 0.36790 (10) | 0.09459 (15) | 0.17945 (6) | 0.01416 (16) | |
| C5 | 0.35026 (11) | −0.08418 (16) | 0.25290 (6) | 0.01607 (17) | |
| H5A | 0.2812 | −0.2171 | 0.2326 | 0.019* | |
| C6 | 0.43785 (11) | −0.05985 (16) | 0.35704 (6) | 0.01649 (16) | |
| H6A | 0.4273 | −0.1791 | 0.4061 | 0.020* | |
| C7 | 0.63122 (10) | 0.15284 (17) | 0.49969 (6) | 0.01611 (17) | |
| H7A | 0.6229 | 0.0242 | 0.5446 | 0.019* | |
| C8 | 0.81013 (9) | 0.34278 (15) | 0.64262 (6) | 0.01427 (16) | |
| C9 | 0.91560 (10) | 0.54613 (15) | 0.66557 (6) | 0.01633 (16) | |
| C10 | 1.01507 (11) | 0.57944 (17) | 0.76609 (7) | 0.01860 (17) | |
| H10A | 1.0854 | 0.7133 | 0.7803 | 0.022* | |
| C11 | 1.00837 (11) | 0.41075 (16) | 0.84506 (7) | 0.01799 (17) | |
| H11A | 1.0752 | 0.4309 | 0.9122 | 0.022* | |
| C12 | 0.90092 (10) | 0.21016 (17) | 0.82364 (6) | 0.01711 (16) | |
| H12A | 0.8951 | 0.0994 | 0.8770 | 0.021* | |
| C13 | 0.80332 (10) | 0.17641 (15) | 0.72308 (6) | 0.01595 (16) | |
| H13A | 0.7331 | 0.0424 | 0.7092 | 0.019* | |
| C14 | 0.19195 (12) | −0.11830 (17) | 0.03898 (7) | 0.02058 (18) | |
| H14A | 0.1551 | −0.1096 | −0.0365 | 0.031* | |
| H14B | 0.0948 | −0.1225 | 0.0720 | 0.031* | |
| H14C | 0.2582 | −0.2615 | 0.0570 | 0.031* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0188 (3) | 0.0212 (3) | 0.0130 (3) | −0.0025 (2) | −0.0003 (2) | −0.0004 (2) |
| O2 | 0.0342 (3) | 0.0193 (3) | 0.0161 (3) | −0.0091 (3) | 0.0045 (2) | 0.0009 (2) |
| N1 | 0.0173 (3) | 0.0180 (4) | 0.0132 (3) | −0.0009 (2) | 0.0019 (3) | −0.0010 (2) |
| C1 | 0.0157 (4) | 0.0152 (3) | 0.0125 (3) | −0.0003 (3) | 0.0023 (3) | −0.0016 (3) |
| C2 | 0.0172 (4) | 0.0142 (3) | 0.0162 (4) | −0.0019 (3) | 0.0024 (3) | −0.0010 (3) |
| C3 | 0.0170 (3) | 0.0146 (3) | 0.0155 (3) | −0.0005 (3) | 0.0021 (3) | 0.0013 (3) |
| C4 | 0.0133 (3) | 0.0159 (4) | 0.0132 (4) | 0.0003 (3) | 0.0026 (3) | −0.0010 (2) |
| C5 | 0.0177 (3) | 0.0163 (4) | 0.0142 (4) | −0.0031 (3) | 0.0030 (3) | −0.0013 (3) |
| C6 | 0.0208 (4) | 0.0158 (3) | 0.0131 (3) | −0.0027 (3) | 0.0039 (3) | −0.0002 (3) |
| C7 | 0.0176 (4) | 0.0178 (4) | 0.0131 (3) | −0.0008 (3) | 0.0032 (3) | −0.0013 (3) |
| C8 | 0.0148 (3) | 0.0150 (3) | 0.0131 (3) | −0.0002 (3) | 0.0029 (3) | −0.0014 (3) |
| C9 | 0.0183 (4) | 0.0166 (3) | 0.0148 (3) | −0.0022 (3) | 0.0050 (3) | −0.0013 (3) |
| C10 | 0.0188 (4) | 0.0196 (4) | 0.0174 (3) | −0.0040 (3) | 0.0036 (3) | −0.0042 (3) |
| C11 | 0.0172 (3) | 0.0220 (4) | 0.0141 (3) | −0.0008 (3) | 0.0013 (3) | −0.0030 (3) |
| C12 | 0.0179 (4) | 0.0184 (4) | 0.0147 (4) | −0.0001 (3) | 0.0025 (3) | 0.0006 (3) |
| C13 | 0.0172 (3) | 0.0162 (4) | 0.0141 (4) | −0.0016 (3) | 0.0023 (3) | −0.0005 (3) |
| C14 | 0.0194 (4) | 0.0224 (4) | 0.0178 (4) | −0.0031 (3) | −0.0015 (3) | −0.0028 (3) |
Geometric parameters (Å, º)
| O1—C4 | 1.3586 (9) | C6—H6A | 0.9300 |
| O1—C14 | 1.4287 (10) | C7—H7A | 0.9300 |
| O2—C9 | 1.3599 (11) | C8—C13 | 1.3973 (11) |
| O2—H1O2 | 0.772 (19) | C8—C9 | 1.4084 (11) |
| N1—C7 | 1.2825 (10) | C9—C10 | 1.3935 (11) |
| N1—C8 | 1.4107 (10) | C10—C11 | 1.3915 (13) |
| C1—C6 | 1.3972 (11) | C10—H10A | 0.9300 |
| C1—C2 | 1.4065 (11) | C11—C12 | 1.4035 (12) |
| C1—C7 | 1.4605 (10) | C11—H11A | 0.9300 |
| C2—C3 | 1.3818 (11) | C12—C13 | 1.3884 (11) |
| C2—H2A | 0.9300 | C12—H12A | 0.9300 |
| C3—C4 | 1.4062 (11) | C13—H13A | 0.9300 |
| C3—H3A | 0.9300 | C14—H14A | 0.9600 |
| C4—C5 | 1.3975 (11) | C14—H14B | 0.9600 |
| C5—C6 | 1.3932 (11) | C14—H14C | 0.9600 |
| C5—H5A | 0.9300 | ||
| C4—O1—C14 | 117.25 (7) | C13—C8—C9 | 118.98 (7) |
| C9—O2—H1O2 | 101.3 (12) | C13—C8—N1 | 127.73 (7) |
| C7—N1—C8 | 121.55 (7) | C9—C8—N1 | 113.29 (7) |
| C6—C1—C2 | 118.64 (7) | O2—C9—C10 | 119.93 (8) |
| C6—C1—C7 | 118.99 (7) | O2—C9—C8 | 119.18 (7) |
| C2—C1—C7 | 122.36 (7) | C10—C9—C8 | 120.88 (7) |
| C3—C2—C1 | 120.54 (7) | C11—C10—C9 | 119.45 (8) |
| C3—C2—H2A | 119.7 | C11—C10—H10A | 120.3 |
| C1—C2—H2A | 119.7 | C9—C10—H10A | 120.3 |
| C2—C3—C4 | 120.07 (8) | C10—C11—C12 | 120.11 (8) |
| C2—C3—H3A | 120.0 | C10—C11—H11A | 119.9 |
| C4—C3—H3A | 120.0 | C12—C11—H11A | 119.9 |
| O1—C4—C5 | 124.37 (7) | C13—C12—C11 | 120.24 (8) |
| O1—C4—C3 | 115.38 (7) | C13—C12—H12A | 119.9 |
| C5—C4—C3 | 120.24 (7) | C11—C12—H12A | 119.9 |
| C6—C5—C4 | 118.88 (7) | C12—C13—C8 | 120.31 (8) |
| C6—C5—H5A | 120.6 | C12—C13—H13A | 119.8 |
| C4—C5—H5A | 120.6 | C8—C13—H13A | 119.8 |
| C5—C6—C1 | 121.63 (8) | O1—C14—H14A | 109.5 |
| C5—C6—H6A | 119.2 | O1—C14—H14B | 109.5 |
| C1—C6—H6A | 119.2 | H14A—C14—H14B | 109.5 |
| N1—C7—C1 | 122.48 (7) | O1—C14—H14C | 109.5 |
| N1—C7—H7A | 118.8 | H14A—C14—H14C | 109.5 |
| C1—C7—H7A | 118.8 | H14B—C14—H14C | 109.5 |
| C6—C1—C2—C3 | −0.41 (12) | C2—C1—C7—N1 | 4.45 (12) |
| C7—C1—C2—C3 | 178.77 (7) | C7—N1—C8—C13 | −6.46 (13) |
| C1—C2—C3—C4 | 0.40 (12) | C7—N1—C8—C9 | 173.81 (7) |
| C14—O1—C4—C5 | −1.14 (12) | C13—C8—C9—O2 | −179.42 (8) |
| C14—O1—C4—C3 | 177.64 (7) | N1—C8—C9—O2 | 0.34 (11) |
| C2—C3—C4—O1 | −178.73 (7) | C13—C8—C9—C10 | 1.49 (12) |
| C2—C3—C4—C5 | 0.10 (12) | N1—C8—C9—C10 | −178.75 (7) |
| O1—C4—C5—C6 | 178.14 (7) | O2—C9—C10—C11 | −179.85 (8) |
| C3—C4—C5—C6 | −0.58 (12) | C8—C9—C10—C11 | −0.77 (13) |
| C4—C5—C6—C1 | 0.57 (13) | C9—C10—C11—C12 | −0.61 (14) |
| C2—C1—C6—C5 | −0.09 (13) | C10—C11—C12—C13 | 1.27 (13) |
| C7—C1—C6—C5 | −179.29 (7) | C11—C12—C13—C8 | −0.54 (13) |
| C8—N1—C7—C1 | −178.67 (8) | C9—C8—C13—C12 | −0.82 (12) |
| C6—C1—C7—N1 | −176.38 (8) | N1—C8—C13—C12 | 179.45 (7) |
Hydrogen-bond geometry (Å, º)
Cg1 and Cg2 are the centroids of rings C1–C6 and C8–C13, respectively.
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H1O2···N1 | 0.774 (18) | 2.078 (17) | 2.6315 (11) | 128.7 (17) |
| C14—H14B···O2i | 0.96 | 2.71 | 3.2876 (12) | 119 |
| C2—H2A···Cg2ii | 0.93 | 2.93 | 3.5662 (9) | 127 |
| C13—H13A···Cg1iii | 0.93 | 2.76 | 3.4671 (9) | 134 |
Symmetry codes: (i) x−1, −y+1, z−1/2; (ii) x, −y+1, z−1/2; (iii) x, −y, z+1/2.
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015008348/su5124sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015008348/su5124Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015008348/su5124Isup3.cml
CCDC reference: 1062128
Additional supporting information: crystallographic information; 3D view; checkCIF report