organic compounds
(E)-2-{[(Furan-2-ylmethyl)imino]methyl}-4-nitrophenol
aChemistry Department, Morgan State University, 1700 East Cold Spring Lane, Baltimore, MD 21251, USA, bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and cDepartment of Chemistry, Keene State College, Keene, NH 03410, USA
*Correspondence e-mail: rbutcher99@yahoo.com
In the title compound, C12H10N2O4, the furan-2-ylmethyl group is disordered over two sets of sites, with refined occupancies of 0.858 (3) and 0.143 (3). In the major component of disorder, the dihedral angle between the furan and benzene rings is 63.1 (2)° and for the minor component this value is 67.9 (6)°. The planes of the nitro group and the attached benzene ring form a dihedral angle of 4.34 (17)°. In the crystal, inversion-related molecules are linked by two pairs of weak C—H⋯O interactions, one involving the nitro group and the other involving the O—H group as an acceptor. As a result of these associations, ribbons are formed along [120]. A strong intramolecular O—H⋯N hydrogen bond is observed.
CCDC reference: 991243
Related literature
For the use of salicylidene compounds as anion sensors, see: Hijji et al. (2009) and for the use of related compounds as anion sensors, see: Hijji et al. (2004). For the bioactivity of metal complexes of structurally related salicylidene derivatives, see: Mandal et al. (2009a,b). For related structures, see: Song et al. (2008); Khalaji et al. (2011a,b).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 991243
10.1107/S1600536814005583/lh5694sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814005583/lh5694Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814005583/lh5694Isup3.cml
The title compound adopts an E configuration with respect to the C═N imine bond. Structurally related salicylidene derivatives have been used as anion sensors (Hijji, et al., 2004; Hijji et al., 2009) and their metal complexes have shown bioactivity (Mandal et al., 2009a,b). Similar structures have been previously reported (Song et al., 2008; Khalaji et al., 2011a,b).
The molecular structure of the title compound is shown in Fig. 1. The furan-2-ylmethyl group is disordered over two sets of sites with refined occupancies of 0.858 (3) and 0.142 (3). In the major component of disorder the dihedral angle between the furan and benzene rings is 63.1 (2)° and for the minor component this value is 67.9 (6)°. The nitro group and attached benzene ring form a dihedral angle of 4.34 (17)°. In the crystal, inversion related molecules are linked by two pairs of weak C—H···O interactions, one involves the nitro group while the other involves the O—H as an acceptor (Fig. 2). As a result of these associations ribbons are formed along [120]. A strong intramolecular O—H···N hydrogen bond is observed.
((E)-2-(((Furan-2-ylmethyl)imino)methyl)-4-nitrophenol was synthesized by mixing 2-methylfurylamine (0.29 g, 3mmol) with 5-nitro-2-hydroxybenzaldehyde. (0.32 g, 2 mmol) the mixture was mixed well and turned dark yellow. After mixing and grinding for 5 minutes the mixture was dissolved in 15 mL of diethyl ether and allowed to crystallize to give yellow crystals, 0.378g, 77% yield), m.p. (393-395 K). A sample was recrystallized from diethyl ether with slow evaporation to provide a crystal suitable for x-ray measurements.
H atoms were placed in geometrically idealized positions with a C—H distances of 0.95 and 0.99 Å Uĩso~(H) = 1.2U~eq~(C) and 0.96 Å for CH~3~ [Uĩso~(H) = 1.5U~eq~(C)]. The furan ring was refined as disordered over two conformations. Both components were constrained to have similar geometries with occupancies of 0.858 (3) and 0.142 (3). For the hydroxy group the H atom was refined isotropically.
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound showing ellipsoids at the 30% probabilty level (major component only). The dashed line indicates a hydrogen bond. | |
Fig. 2. Packing diagram for the complex viewed along the c axis showing the repeating motif forming ribbons along [1 2 0]. N—H···O hydrogen bonds and C—H···O interactions shown by dashed lines. |
C12H10N2O4 | Z = 2 |
Mr = 246.22 | F(000) = 256 |
Triclinic, P1 | Dx = 1.480 Mg m−3 |
a = 5.4427 (7) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 8.2488 (10) Å | Cell parameters from 2639 reflections |
c = 12.4701 (14) Å | θ = 3.6–75.5° |
α = 98.901 (9)° | µ = 0.96 mm−1 |
β = 92.04 (1)° | T = 123 K |
γ = 91.69 (1)° | Prism, pale yellow |
V = 552.41 (12) Å3 | 0.34 × 0.26 × 0.17 mm |
Agilent Xcalibur (Ruby, Gemini) diffractometer | 2047 reflections with I > 2σ(I) |
Detector resolution: 10.5081 pixels mm-1 | Rint = 0.019 |
ω scans | θmax = 75.6°, θmin = 3.6° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | h = −6→6 |
Tmin = 0.912, Tmax = 1.000 | k = −10→10 |
3400 measured reflections | l = −11→15 |
2210 independent reflections |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0764P)2 + 0.0922P] where P = (Fo2 + 2Fc2)/3 |
2210 reflections | (Δ/σ)max < 0.001 |
186 parameters | Δρmax = 0.32 e Å−3 |
13 restraints | Δρmin = −0.27 e Å−3 |
C12H10N2O4 | γ = 91.69 (1)° |
Mr = 246.22 | V = 552.41 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.4427 (7) Å | Cu Kα radiation |
b = 8.2488 (10) Å | µ = 0.96 mm−1 |
c = 12.4701 (14) Å | T = 123 K |
α = 98.901 (9)° | 0.34 × 0.26 × 0.17 mm |
β = 92.04 (1)° |
Agilent Xcalibur (Ruby, Gemini) diffractometer | 2210 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 2047 reflections with I > 2σ(I) |
Tmin = 0.912, Tmax = 1.000 | Rint = 0.019 |
3400 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 13 restraints |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.32 e Å−3 |
2210 reflections | Δρmin = −0.27 e Å−3 |
186 parameters |
Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. 1H-NMR (400 MHz): d ppm (CDCl3): 14.41(br. s 1H), 8.39 (t, J = 1.25 Hz, 1H) 8.255 (d, J = 2.85 Hz, 1H), 8.205 (dd, J = 8.25, 2.85 Hz, 1H), 7.44 ( dd, J = 1.75, 0.75 Hz, 1H), 7.01 ( d, J = 7.30 Hz, 1H), 6.395 (dd, J = 3.45, 1.85 Hz, 1H), 6.35 dt, J = 3.45, 0.75 Hz, 1 H), 4.84 (s, 2 H). 13C-NMR (100 MHz) d ppm (CDCl3): 167.64, 164.96, 149.57, 143.12, 139.45, 128.23, 128.08, 118.46, 117.44, 110.05, 108.99, 54.01. Mass spec: M+ = 246. |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.24922 (16) | 0.42490 (11) | 0.60178 (7) | 0.0282 (2) | |
H1O | 0.352 (5) | 0.424 (3) | 0.665 (2) | 0.082 (8)* | |
O2 | 0.51829 (18) | 0.00193 (12) | 0.16611 (7) | 0.0345 (2) | |
O3 | 0.83082 (19) | −0.04412 (13) | 0.26772 (8) | 0.0406 (3) | |
N1 | 0.6361 (2) | 0.02267 (13) | 0.25331 (9) | 0.0281 (2) | |
N2 | 0.6077 (2) | 0.34958 (13) | 0.72346 (8) | 0.0281 (2) | |
C1 | 0.3478 (2) | 0.33032 (14) | 0.51862 (9) | 0.0226 (2) | |
C2 | 0.2310 (2) | 0.31430 (15) | 0.41515 (10) | 0.0244 (2) | |
H2A | 0.0863 | 0.3727 | 0.4049 | 0.029* | |
C3 | 0.3249 (2) | 0.21438 (14) | 0.32834 (9) | 0.0242 (2) | |
H3A | 0.2450 | 0.2024 | 0.2585 | 0.029* | |
C4 | 0.5397 (2) | 0.13099 (14) | 0.34469 (9) | 0.0233 (2) | |
C5 | 0.6607 (2) | 0.14649 (14) | 0.44537 (10) | 0.0240 (2) | |
H5A | 0.8072 | 0.0893 | 0.4542 | 0.029* | |
C6 | 0.5667 (2) | 0.24627 (14) | 0.53369 (9) | 0.0222 (2) | |
C7 | 0.6911 (2) | 0.26050 (14) | 0.64088 (10) | 0.0256 (3) | |
H7A | 0.8368 | 0.2022 | 0.6491 | 0.031* | |
O4 | 0.6949 (2) | 0.62761 (19) | 0.92624 (12) | 0.0322 (3) | 0.858 (3) |
C8 | 0.7459 (4) | 0.3535 (3) | 0.8281 (2) | 0.0320 (5) | 0.858 (3) |
H8A | 0.8813 | 0.2757 | 0.8180 | 0.038* | 0.858 (3) |
H8B | 0.6350 | 0.3170 | 0.8816 | 0.038* | 0.858 (3) |
C9 | 0.8503 (5) | 0.5208 (3) | 0.8716 (3) | 0.0253 (3) | 0.858 (3) |
C10 | 1.0759 (3) | 0.5895 (2) | 0.87026 (14) | 0.0297 (4) | 0.858 (3) |
H10A | 1.2147 | 0.5405 | 0.8362 | 0.036* | 0.858 (3) |
C11 | 1.0658 (4) | 0.7526 (2) | 0.93068 (14) | 0.0318 (4) | 0.858 (3) |
H11A | 1.1970 | 0.8325 | 0.9449 | 0.038* | 0.858 (3) |
C12 | 0.8342 (4) | 0.76926 (19) | 0.96289 (13) | 0.0328 (4) | 0.858 (3) |
H12A | 0.7744 | 0.8649 | 1.0049 | 0.039* | 0.858 (3) |
O4A | 0.7528 (18) | 0.6486 (14) | 0.9445 (9) | 0.0322 (3) | 0.142 (3) |
C8A | 0.694 (3) | 0.3590 (19) | 0.8374 (16) | 0.0320 (5) | 0.142 (3) |
H8A1 | 0.8057 | 0.2681 | 0.8444 | 0.038* | 0.142 (3) |
H8A2 | 0.5526 | 0.3481 | 0.8836 | 0.038* | 0.142 (3) |
C9A | 0.827 (3) | 0.519 (2) | 0.8736 (17) | 0.0253 (3) | 0.142 (3) |
C10A | 1.0441 (18) | 0.5434 (14) | 0.8316 (9) | 0.0297 (4) | 0.142 (3) |
H10B | 1.1253 | 0.4736 | 0.7772 | 0.036* | 0.142 (3) |
C11A | 1.1230 (19) | 0.6970 (14) | 0.8873 (9) | 0.0318 (4) | 0.142 (3) |
H11B | 1.2789 | 0.7477 | 0.8793 | 0.038* | 0.142 (3) |
C12A | 0.950 (3) | 0.7651 (13) | 0.9539 (9) | 0.0328 (4) | 0.142 (3) |
H12B | 0.9601 | 0.8700 | 0.9981 | 0.039* | 0.142 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0281 (4) | 0.0311 (4) | 0.0245 (4) | 0.0086 (3) | 0.0018 (3) | 0.0001 (3) |
O2 | 0.0409 (5) | 0.0361 (5) | 0.0247 (4) | 0.0025 (4) | 0.0013 (4) | −0.0014 (4) |
O3 | 0.0365 (5) | 0.0429 (6) | 0.0409 (5) | 0.0172 (4) | 0.0048 (4) | −0.0024 (4) |
N1 | 0.0291 (5) | 0.0253 (5) | 0.0298 (5) | 0.0021 (4) | 0.0052 (4) | 0.0034 (4) |
N2 | 0.0347 (5) | 0.0247 (5) | 0.0245 (5) | 0.0003 (4) | −0.0056 (4) | 0.0040 (4) |
C1 | 0.0220 (5) | 0.0210 (5) | 0.0252 (5) | 0.0008 (4) | 0.0021 (4) | 0.0048 (4) |
C2 | 0.0205 (5) | 0.0249 (5) | 0.0283 (6) | 0.0036 (4) | −0.0002 (4) | 0.0059 (4) |
C3 | 0.0243 (5) | 0.0261 (5) | 0.0229 (5) | −0.0002 (4) | −0.0010 (4) | 0.0063 (4) |
C4 | 0.0246 (5) | 0.0203 (5) | 0.0249 (6) | 0.0009 (4) | 0.0038 (4) | 0.0027 (4) |
C5 | 0.0212 (5) | 0.0209 (5) | 0.0308 (6) | 0.0030 (4) | 0.0016 (4) | 0.0067 (4) |
C6 | 0.0225 (5) | 0.0202 (5) | 0.0244 (5) | 0.0003 (4) | −0.0007 (4) | 0.0054 (4) |
C7 | 0.0263 (5) | 0.0211 (5) | 0.0299 (6) | 0.0011 (4) | −0.0047 (4) | 0.0064 (4) |
O4 | 0.0284 (7) | 0.0340 (6) | 0.0326 (7) | 0.0038 (5) | 0.0018 (5) | −0.0002 (5) |
C8 | 0.0410 (13) | 0.0279 (6) | 0.0266 (8) | 0.0046 (8) | −0.0087 (8) | 0.0042 (5) |
C9 | 0.0277 (8) | 0.0287 (6) | 0.0195 (5) | 0.0067 (5) | −0.0021 (5) | 0.0030 (4) |
C10 | 0.0246 (7) | 0.0411 (10) | 0.0230 (8) | 0.0050 (6) | 0.0016 (6) | 0.0032 (7) |
C11 | 0.0386 (9) | 0.0338 (9) | 0.0222 (8) | −0.0078 (7) | −0.0049 (7) | 0.0047 (6) |
C12 | 0.0441 (10) | 0.0261 (7) | 0.0268 (7) | 0.0069 (7) | −0.0003 (7) | −0.0011 (5) |
O4A | 0.0284 (7) | 0.0340 (6) | 0.0326 (7) | 0.0038 (5) | 0.0018 (5) | −0.0002 (5) |
C8A | 0.0410 (13) | 0.0279 (6) | 0.0266 (8) | 0.0046 (8) | −0.0087 (8) | 0.0042 (5) |
C9A | 0.0277 (8) | 0.0287 (6) | 0.0195 (5) | 0.0067 (5) | −0.0021 (5) | 0.0030 (4) |
C10A | 0.0246 (7) | 0.0411 (10) | 0.0230 (8) | 0.0050 (6) | 0.0016 (6) | 0.0032 (7) |
C11A | 0.0386 (9) | 0.0338 (9) | 0.0222 (8) | −0.0078 (7) | −0.0049 (7) | 0.0047 (6) |
C12A | 0.0441 (10) | 0.0261 (7) | 0.0268 (7) | 0.0069 (7) | −0.0003 (7) | −0.0011 (5) |
O1—C1 | 1.3363 (14) | C8—C9 | 1.491 (3) |
O1—H1O | 0.95 (3) | C8—H8A | 0.9900 |
O2—N1 | 1.2286 (15) | C8—H8B | 0.9900 |
O3—N1 | 1.2289 (15) | C9—C10 | 1.339 (3) |
N1—C4 | 1.4586 (15) | C10—C11 | 1.440 (3) |
N2—C7 | 1.2747 (17) | C10—H10A | 0.9500 |
N2—C8A | 1.47 (2) | C11—C12 | 1.341 (3) |
N2—C8 | 1.479 (3) | C11—H11A | 0.9500 |
C1—C2 | 1.4036 (16) | C12—H12A | 0.9500 |
C1—C6 | 1.4172 (16) | O4A—C9A | 1.359 (14) |
C2—C3 | 1.3788 (17) | O4A—C12A | 1.410 (14) |
C2—H2A | 0.9500 | C8A—C9A | 1.483 (14) |
C3—C4 | 1.3982 (17) | C8A—H8A1 | 0.9900 |
C3—H3A | 0.9500 | C8A—H8A2 | 0.9900 |
C4—C5 | 1.3830 (17) | C9A—C10A | 1.333 (14) |
C5—C6 | 1.3917 (17) | C10A—C11A | 1.395 (12) |
C5—H5A | 0.9500 | C10A—H10B | 0.9500 |
C6—C7 | 1.4633 (16) | C11A—C12A | 1.354 (13) |
C7—H7A | 0.9500 | C11A—H11B | 0.9500 |
O4—C9 | 1.362 (3) | C12A—H12B | 0.9500 |
O4—C12 | 1.381 (2) | ||
C1—O1—H1O | 108.3 (17) | H8A—C8—H8B | 107.9 |
O2—N1—O3 | 123.29 (11) | C10—C9—O4 | 111.09 (19) |
O2—N1—C4 | 118.49 (10) | C10—C9—C8 | 132.3 (2) |
O3—N1—C4 | 118.22 (11) | O4—C9—C8 | 116.55 (19) |
C7—N2—C8A | 127.0 (7) | C9—C10—C11 | 106.24 (16) |
C7—N2—C8 | 116.83 (12) | C9—C10—H10A | 126.9 |
O1—C1—C2 | 119.08 (10) | C11—C10—H10A | 126.9 |
O1—C1—C6 | 120.99 (10) | C12—C11—C10 | 106.29 (14) |
C2—C1—C6 | 119.92 (11) | C12—C11—H11A | 126.9 |
C3—C2—C1 | 120.40 (11) | C10—C11—H11A | 126.9 |
C3—C2—H2A | 119.8 | C11—C12—O4 | 110.34 (14) |
C1—C2—H2A | 119.8 | C11—C12—H12A | 124.8 |
C2—C3—C4 | 119.02 (11) | O4—C12—H12A | 124.8 |
C2—C3—H3A | 120.5 | C9A—O4A—C12A | 104.9 (10) |
C4—C3—H3A | 120.5 | N2—C8A—C9A | 109.4 (15) |
C5—C4—C3 | 121.81 (11) | N2—C8A—H8A1 | 109.8 |
C5—C4—N1 | 119.21 (10) | C9A—C8A—H8A1 | 109.8 |
C3—C4—N1 | 118.97 (11) | N2—C8A—H8A2 | 109.8 |
C4—C5—C6 | 119.65 (11) | C9A—C8A—H8A2 | 109.8 |
C4—C5—H5A | 120.2 | H8A1—C8A—H8A2 | 108.2 |
C6—C5—H5A | 120.2 | C10A—C9A—O4A | 114.2 (11) |
C5—C6—C1 | 119.19 (11) | C10A—C9A—C8A | 117.8 (13) |
C5—C6—C7 | 119.90 (10) | O4A—C9A—C8A | 128.0 (13) |
C1—C6—C7 | 120.90 (11) | C9A—C10A—C11A | 102.9 (10) |
N2—C7—C6 | 121.28 (11) | C9A—C10A—H10B | 128.6 |
N2—C7—H7A | 119.4 | C11A—C10A—H10B | 128.6 |
C6—C7—H7A | 119.4 | C12A—C11A—C10A | 111.8 (9) |
C9—O4—C12 | 106.02 (16) | C12A—C11A—H11B | 124.1 |
N2—C8—C9 | 112.0 (2) | C10A—C11A—H11B | 124.1 |
N2—C8—H8A | 109.2 | C11A—C12A—O4A | 106.0 (9) |
C9—C8—H8A | 109.2 | C11A—C12A—H12B | 127.0 |
N2—C8—H8B | 109.2 | O4A—C12A—H12B | 127.0 |
C9—C8—H8B | 109.2 | ||
O1—C1—C2—C3 | −178.40 (10) | C8A—N2—C8—C9 | −94 (3) |
C6—C1—C2—C3 | 1.40 (18) | C12—O4—C9—C10 | −1.4 (3) |
C1—C2—C3—C4 | −0.77 (18) | C12—O4—C9—C8 | 177.1 (3) |
C2—C3—C4—C5 | −0.24 (18) | N2—C8—C9—C10 | −100.0 (4) |
C2—C3—C4—N1 | 178.74 (10) | N2—C8—C9—O4 | 81.9 (3) |
O2—N1—C4—C5 | 175.41 (10) | O4—C9—C10—C11 | 1.2 (3) |
O3—N1—C4—C5 | −4.15 (17) | C8—C9—C10—C11 | −177.0 (4) |
O2—N1—C4—C3 | −3.60 (17) | C9—C10—C11—C12 | −0.4 (2) |
O3—N1—C4—C3 | 176.84 (11) | C10—C11—C12—O4 | −0.44 (18) |
C3—C4—C5—C6 | 0.62 (18) | C9—O4—C12—C11 | 1.1 (2) |
N1—C4—C5—C6 | −178.37 (10) | C7—N2—C8A—C9A | 108.4 (12) |
C4—C5—C6—C1 | 0.02 (17) | C8—N2—C8A—C9A | 74 (3) |
C4—C5—C6—C7 | 178.74 (10) | C12A—O4A—C9A—C10A | −4 (2) |
O1—C1—C6—C5 | 178.78 (10) | C12A—O4A—C9A—C8A | 177 (2) |
C2—C1—C6—C5 | −1.01 (17) | N2—C8A—C9A—C10A | −70 (2) |
O1—C1—C6—C7 | 0.07 (17) | N2—C8A—C9A—O4A | 109 (2) |
C2—C1—C6—C7 | −179.72 (10) | O4A—C9A—C10A—C11A | 5 (2) |
C8A—N2—C7—C6 | 171.7 (8) | C8A—C9A—C10A—C11A | −176.2 (18) |
C8—N2—C7—C6 | 179.22 (13) | C9A—C10A—C11A—C12A | −4.2 (16) |
C5—C6—C7—N2 | −179.25 (11) | C10A—C11A—C12A—O4A | 2.1 (13) |
C1—C6—C7—N2 | −0.55 (18) | C9A—O4A—C12A—C11A | 0.9 (16) |
C7—N2—C8—C9 | 116.69 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N2 | 0.95 (3) | 1.72 (3) | 2.5784 (14) | 148 (2) |
C2—H2A···O1i | 0.95 | 2.52 | 3.4548 (16) | 169 |
C7—H7A···O3ii | 0.95 | 2.54 | 3.4567 (16) | 161 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+2, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N2 | 0.95 (3) | 1.72 (3) | 2.5784 (14) | 148 (2) |
C2—H2A···O1i | 0.95 | 2.52 | 3.4548 (16) | 168.7 |
C7—H7A···O3ii | 0.95 | 2.54 | 3.4567 (16) | 161.0 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+2, −y, −z+1. |
Footnotes
‡Current Address: Department of Chemistry and Earth Sciences, Qatar University, PO Box 2713, Doha, Qatar.
Acknowledgements
RJB wishes to acknowledge the National Science Foundation MRI program (CHE0619278) for funds to purchase the diffractometer and the Howard University Nanoscience Facility for access to liquid nitrogen. YH would like to thank the Department of Chemistry and Earth Sciences at Qatar University for support.
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