organic compounds
(E)-2-[(Pyren-1-ylimino)methyl]quinolin-8-ol
aDepartment of Environmental Science, University of Kalyani, Nadia Kalyani 741 235, West Bengal, India, and bInstitute of Physics, University of Neuchâtel, rue Emile-Argand11, CH-2000 Neuchâtel, Switzerland
*Correspondence e-mail: helen.stoeckli-evans@unine.ch
In the title compound, C26H16N2O, the pyrene ring system (r.m.s. deviation = 0.021 Å) is inclined to the planar quinoline ring system (r.m.s. deviation = 0.017 Å) by 30.62 (5)°, and the conformation about the bridging N=C bond is E. There is an intramolecular O—H⋯N hydrogen bond with an S(5) ring motif present. In the crystal, molecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers with an R22(14) ring motif, flanked by two R21(7) ring motifs. The dimers stack along the b axis with slipped parallel π–π interactions involving neighbouring molecules; the shortest π–π interaction involves aromatic rings of the quinoline ring system [inter-centroid distance = 3.6267 (11) Å].
Keywords: crystal structure; pyrene; fluorescence sensor; hydrogen bonding.
CCDC reference: 1471583
Structure description
The title compound has recently been shown to act as a reversible pyrene-based turn-on luminescent chemosensor for the selective detection of Fe3+ in an aqueous environment (Mukherjee & Talukder, 2016).
In the title compound, Fig. 1, the pyrene ring system (C1–C16) is planar (r.m.s. deviation = 0.021 Å) and it is inclined to the planar quinoline ring system (N2/C18–C26; r.m.s. deviation = 0.017 Å) by 30.62 (5)°. The conformation about the N1=C17 bond is E and there is an intramolecular O—H⋯N hydrogen bond with an S(5) ring motif present (Fig. 1 and Table 1).
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In the crystal, molecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers with an (14) ring motif, flanked by two (7) ring motifs (Fig. 2 and Table 1). The dimers stack along the b axis with slipped parallel π–π interactions involving neighbouring molecules (Fig. 3); the shortest π–π interaction involves aromatic rings (N2/C18–C21/C26) and (C21–C26) of the quinoline ring system [Cg1⋯Cg6i = 3.6267 (11) Å, interplanar distance = 3.466 (1) Å, slippage = 1.078 Å, symmetry code: (i) x, y + 1, z; where Cg1 and Cg6 are the centroids of rings (N2/C18–C21/C26) and (C21–C26), respectively].
Synthesis and crystallization
The title compound was synthesized by a 1:1 condensation of 8-hydroxyquinoline-2-carboxaldehyde and 1-aminopyrene in methanol, and characterized by 1H NMR, 13C NMR, FTIR and UV–Vis spectroscopic studies as reported on recently (Mukherjee & Talukder, 2016). Brown rod-like crystals were obtained by slow evaporation of a solution in methanol.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1471583
10.1107/S2414314616005435/zp4006sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616005435/zp4006Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616005435/zp4006Isup3.cml
The title compound was synthesized by a 1:1 condensation of 8-hydroxyquinoline-2-carboxaldehyde and 1-aminopyrene in methanol, and characterized by 1H NMR, 13C NMR, FTIR and UV–Vis spectroscopic studies as reported on recently (Mukherjee & Talukder, 2016). Brown rod-like crystals were obtained by slow evaporation of a solution in methanol.
The title compound has recently been shown to act as a reversible pyrene-based turn-on luminescent chemosensor for the selective detection of Fe3+ in an aqueous environment (Mukherjee & Talukder, 2016).
In the title compound, Fig. 1, the pyrene ring system (C1–C16) is planar (r.m.s. deviation = 0.021 Å) and it is inclined to the planar quinoline ring system (N2/C18–C26; r.m.s. deviation = 0.017 Å) by 30.62 (5)°. The conformation about the N1═C17 bond is E and there is an intramolecular O—H···N hydrogen bond with an S(5) ring motif present (Fig. 1 and Table 1).
In the crystal, molecules are linked by pairs of C—H···O hydrogen bonds, forming inversion dimers with an R22(14) ring motif, flanked by two R21(7) ring motifs (Fig. 2 and Table 1). The dimers stack up the b axis with slipped parallel π–π interactions involving neighbouring molecules (Fig. 3); the shortest π–π interaction involves aromatic rings (N2/C18–C21/C26) and (C21–C26) of the quinoline ring system [Cg1···Cg6i = 3.6267 (11) Å, interplanar distance = 3.466 (1) Å, slippage = 1.078 Å, symmetry code: (i) x, y + 1, z; where Cg1 and Cg6 are the centroids of rings (N2/C18–C21/C26) and (C21–C26), respectively].
Data collection: X-AREA (Stoe & Cie, 2009); cell
X-AREA (Stoe & Cie, 2009); data reduction: X-RED32 (Stoe & Cie, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).Fig. 1. A view of the molecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular O—H···N hydrogen bond is shown as a dashed line (see Table 1). | |
Fig. 2. A view of the inversion dimer formed by pairs of C—H···O hydrogen bonds (dashed lines; see Table 1). H atoms not involved in these interactions have been omitted for clarity. | |
Fig. 3. A view along the a axis of the crystal packing of the title compound. Hydrogen bonds are shown as a dashed lines (see Table 1), and H atoms not involved in these interactions have been omitted for clarity. |
C26H16N2O | F(000) = 776 |
Mr = 372.41 | Dx = 1.387 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.9840 (19) Å | Cell parameters from 7937 reflections |
b = 4.8453 (3) Å | θ = 1.3–26.7° |
c = 23.071 (3) Å | µ = 0.09 mm−1 |
β = 93.835 (9)° | T = 203 K |
V = 1782.8 (3) Å3 | Rod, brown |
Z = 4 | 0.50 × 0.27 × 0.10 mm |
Stoe IPDS 2 diffractometer | 2092 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.075 |
Plane graphite monochromator | θmax = 26.3°, θmin = 1.3° |
φ + ω scans | h = −19→17 |
17513 measured reflections | k = −6→5 |
3558 independent reflections | l = −28→28 |
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)] = 0.040 | Hydrogen site location: mixed |
wR(F2) = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.88 | w = 1/[σ2(Fo2) + (0.0438P)2] where P = (Fo2 + 2Fc2)/3 |
3558 reflections | (Δ/σ)max < 0.001 |
265 parameters | Δρmax = 0.16 e Å−3 |
1 restraint | Δρmin = −0.12 e Å−3 |
C26H16N2O | V = 1782.8 (3) Å3 |
Mr = 372.41 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.9840 (19) Å | µ = 0.09 mm−1 |
b = 4.8453 (3) Å | T = 203 K |
c = 23.071 (3) Å | 0.50 × 0.27 × 0.10 mm |
β = 93.835 (9)° |
Stoe IPDS 2 diffractometer | 2092 reflections with I > 2σ(I) |
17513 measured reflections | Rint = 0.075 |
3558 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | 1 restraint |
wR(F2) = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.88 | Δρmax = 0.16 e Å−3 |
3558 reflections | Δρmin = −0.12 e Å−3 |
265 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.00534 (9) | −0.8729 (3) | 0.43353 (6) | 0.0610 (4) | |
H1O | 0.0175 (14) | −0.737 (4) | 0.4572 (9) | 0.091* | |
N1 | 0.24740 (9) | 0.0215 (3) | 0.50451 (6) | 0.0396 (4) | |
N2 | 0.11816 (9) | −0.5020 (3) | 0.43966 (6) | 0.0383 (3) | |
C1 | 0.25103 (11) | 0.1993 (3) | 0.55347 (7) | 0.0371 (4) | |
C2 | 0.18087 (11) | 0.2776 (4) | 0.58217 (7) | 0.0416 (4) | |
H2 | 0.1284 | 0.1990 | 0.5712 | 0.050* | |
C3 | 0.18745 (11) | 0.4697 (4) | 0.62665 (7) | 0.0422 (4) | |
H3 | 0.1393 | 0.5183 | 0.6456 | 0.051* | |
C4 | 0.26386 (11) | 0.5926 (3) | 0.64404 (7) | 0.0385 (4) | |
C5 | 0.27221 (12) | 0.8001 (4) | 0.68850 (7) | 0.0449 (5) | |
H5 | 0.2248 | 0.8528 | 0.7078 | 0.054* | |
C6 | 0.34677 (13) | 0.9210 (4) | 0.70319 (7) | 0.0474 (5) | |
H6 | 0.3500 | 1.0570 | 0.7323 | 0.057* | |
C7 | 0.42106 (12) | 0.8468 (3) | 0.67542 (7) | 0.0399 (4) | |
C8 | 0.49893 (13) | 0.9696 (4) | 0.68975 (8) | 0.0494 (5) | |
H8 | 0.5034 | 1.1074 | 0.7185 | 0.059* | |
C9 | 0.56911 (13) | 0.8912 (4) | 0.66230 (8) | 0.0509 (5) | |
H9 | 0.6210 | 0.9755 | 0.6726 | 0.061* | |
C10 | 0.56414 (12) | 0.6905 (4) | 0.61980 (8) | 0.0473 (5) | |
H10 | 0.6126 | 0.6407 | 0.6014 | 0.057* | |
C11 | 0.48832 (11) | 0.5606 (3) | 0.60381 (7) | 0.0391 (4) | |
C12 | 0.47988 (12) | 0.3507 (4) | 0.56009 (7) | 0.0429 (4) | |
H12 | 0.5279 | 0.2912 | 0.5423 | 0.051* | |
C13 | 0.40516 (11) | 0.2356 (4) | 0.54364 (7) | 0.0408 (4) | |
H13 | 0.4022 | 0.1014 | 0.5141 | 0.049* | |
C14 | 0.33014 (11) | 0.3141 (3) | 0.57034 (7) | 0.0351 (4) | |
C15 | 0.33661 (11) | 0.5137 (3) | 0.61542 (7) | 0.0355 (4) | |
C16 | 0.41497 (11) | 0.6392 (3) | 0.63201 (7) | 0.0366 (4) | |
C17 | 0.18879 (11) | −0.1557 (3) | 0.49708 (7) | 0.0403 (4) | |
H17 | 0.1504 | −0.1802 | 0.5258 | 0.048* | |
C18 | 0.18104 (11) | −0.3225 (3) | 0.44361 (7) | 0.0362 (4) | |
C19 | 0.23649 (11) | −0.2867 (4) | 0.39939 (7) | 0.0417 (4) | |
H19 | 0.2809 | −0.1599 | 0.4043 | 0.050* | |
C20 | 0.22571 (12) | −0.4362 (4) | 0.34949 (7) | 0.0436 (4) | |
H20 | 0.2624 | −0.4121 | 0.3197 | 0.052* | |
C21 | 0.15907 (11) | −0.6278 (3) | 0.34257 (7) | 0.0387 (4) | |
C22 | 0.14091 (12) | −0.7905 (4) | 0.29233 (7) | 0.0464 (5) | |
H22 | 0.1744 | −0.7761 | 0.2605 | 0.056* | |
C23 | 0.07445 (12) | −0.9689 (4) | 0.29029 (8) | 0.0474 (5) | |
H23 | 0.0625 | −1.0744 | 0.2566 | 0.057* | |
C24 | 0.02363 (12) | −0.9985 (4) | 0.33712 (8) | 0.0487 (5) | |
H24 | −0.0217 | −1.1227 | 0.3348 | 0.058* | |
C25 | 0.04069 (11) | −0.8446 (4) | 0.38630 (8) | 0.0430 (4) | |
C26 | 0.10779 (11) | −0.6530 (3) | 0.38955 (7) | 0.0377 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0568 (9) | 0.0638 (10) | 0.0638 (9) | −0.0192 (8) | 0.0142 (7) | −0.0138 (7) |
N1 | 0.0470 (9) | 0.0346 (8) | 0.0369 (8) | −0.0014 (7) | −0.0005 (7) | −0.0030 (6) |
N2 | 0.0409 (9) | 0.0340 (8) | 0.0397 (8) | 0.0012 (7) | 0.0001 (6) | −0.0018 (6) |
C1 | 0.0468 (11) | 0.0312 (9) | 0.0331 (9) | −0.0013 (8) | 0.0009 (8) | 0.0000 (7) |
C2 | 0.0454 (11) | 0.0398 (10) | 0.0396 (9) | −0.0016 (8) | 0.0025 (8) | −0.0037 (8) |
C3 | 0.0432 (11) | 0.0421 (10) | 0.0417 (10) | 0.0037 (9) | 0.0067 (8) | −0.0007 (8) |
C4 | 0.0491 (11) | 0.0332 (9) | 0.0335 (9) | 0.0016 (8) | 0.0050 (8) | 0.0010 (7) |
C5 | 0.0566 (12) | 0.0414 (10) | 0.0374 (9) | 0.0035 (9) | 0.0071 (8) | −0.0050 (8) |
C6 | 0.0683 (14) | 0.0394 (10) | 0.0344 (9) | −0.0015 (10) | 0.0023 (9) | −0.0049 (8) |
C7 | 0.0522 (11) | 0.0339 (10) | 0.0328 (9) | −0.0033 (8) | −0.0025 (8) | 0.0043 (7) |
C8 | 0.0660 (14) | 0.0415 (11) | 0.0393 (10) | −0.0100 (10) | −0.0074 (10) | 0.0034 (8) |
C9 | 0.0517 (12) | 0.0491 (12) | 0.0502 (11) | −0.0115 (10) | −0.0092 (9) | 0.0093 (9) |
C10 | 0.0460 (11) | 0.0452 (11) | 0.0498 (10) | 0.0009 (9) | −0.0023 (8) | 0.0091 (9) |
C11 | 0.0439 (11) | 0.0337 (9) | 0.0390 (9) | 0.0014 (8) | −0.0022 (8) | 0.0080 (8) |
C12 | 0.0469 (11) | 0.0399 (10) | 0.0420 (10) | 0.0061 (9) | 0.0045 (8) | 0.0047 (8) |
C13 | 0.0526 (12) | 0.0335 (9) | 0.0362 (9) | 0.0022 (8) | 0.0036 (8) | −0.0020 (7) |
C14 | 0.0448 (11) | 0.0287 (9) | 0.0318 (8) | 0.0016 (8) | 0.0025 (7) | 0.0039 (7) |
C15 | 0.0462 (11) | 0.0280 (9) | 0.0319 (8) | 0.0022 (8) | −0.0004 (7) | 0.0043 (7) |
C16 | 0.0480 (11) | 0.0285 (9) | 0.0326 (8) | 0.0005 (8) | −0.0015 (7) | 0.0074 (7) |
C17 | 0.0472 (11) | 0.0360 (10) | 0.0375 (9) | 0.0005 (8) | 0.0013 (8) | −0.0014 (8) |
C18 | 0.0390 (10) | 0.0308 (9) | 0.0381 (9) | 0.0023 (8) | −0.0022 (7) | 0.0005 (7) |
C19 | 0.0443 (11) | 0.0410 (10) | 0.0395 (9) | −0.0057 (8) | 0.0004 (8) | −0.0014 (8) |
C20 | 0.0498 (11) | 0.0431 (10) | 0.0382 (10) | −0.0040 (9) | 0.0056 (8) | −0.0002 (8) |
C21 | 0.0455 (11) | 0.0334 (9) | 0.0364 (9) | 0.0048 (8) | −0.0038 (8) | 0.0008 (7) |
C22 | 0.0602 (13) | 0.0410 (10) | 0.0377 (10) | −0.0006 (9) | 0.0010 (9) | −0.0001 (8) |
C23 | 0.0592 (13) | 0.0406 (10) | 0.0409 (10) | −0.0005 (9) | −0.0087 (9) | −0.0063 (8) |
C24 | 0.0494 (12) | 0.0435 (11) | 0.0521 (11) | −0.0056 (9) | −0.0049 (9) | −0.0048 (9) |
C25 | 0.0416 (11) | 0.0414 (11) | 0.0458 (10) | −0.0001 (9) | 0.0016 (8) | −0.0015 (8) |
C26 | 0.0419 (10) | 0.0306 (9) | 0.0398 (9) | 0.0043 (8) | −0.0046 (8) | 0.0003 (7) |
O1—C25 | 1.362 (2) | C10—H10 | 0.9400 |
O1—H1O | 0.914 (16) | C11—C16 | 1.430 (2) |
N1—C17 | 1.274 (2) | C11—C12 | 1.433 (2) |
N1—C1 | 1.418 (2) | C12—C13 | 1.349 (2) |
N2—C18 | 1.328 (2) | C12—H12 | 0.9400 |
N2—C26 | 1.369 (2) | C13—C14 | 1.436 (2) |
C1—C2 | 1.393 (2) | C13—H13 | 0.9400 |
C1—C14 | 1.412 (2) | C14—C15 | 1.419 (2) |
C2—C3 | 1.384 (2) | C15—C16 | 1.422 (2) |
C2—H2 | 0.9400 | C17—C18 | 1.473 (2) |
C3—C4 | 1.393 (2) | C17—H17 | 0.9400 |
C3—H3 | 0.9400 | C18—C19 | 1.406 (2) |
C4—C15 | 1.427 (2) | C19—C20 | 1.361 (2) |
C4—C5 | 1.436 (2) | C19—H19 | 0.9400 |
C5—C6 | 1.351 (3) | C20—C21 | 1.414 (2) |
C5—H5 | 0.9400 | C20—H20 | 0.9400 |
C6—C7 | 1.432 (2) | C21—C26 | 1.407 (2) |
C6—H6 | 0.9400 | C21—C22 | 1.416 (2) |
C7—C8 | 1.399 (2) | C22—C23 | 1.368 (3) |
C7—C16 | 1.418 (2) | C22—H22 | 0.9400 |
C8—C9 | 1.378 (3) | C23—C24 | 1.402 (2) |
C8—H8 | 0.9400 | C23—H23 | 0.9400 |
C9—C10 | 1.379 (3) | C24—C25 | 1.370 (2) |
C9—H9 | 0.9400 | C24—H24 | 0.9400 |
C10—C11 | 1.393 (2) | C25—C26 | 1.416 (2) |
C25—O1—H1O | 100.9 (15) | C14—C13—H13 | 119.4 |
C17—N1—C1 | 120.46 (15) | C1—C14—C15 | 119.39 (15) |
C18—N2—C26 | 117.16 (14) | C1—C14—C13 | 122.38 (15) |
C2—C1—C14 | 119.75 (15) | C15—C14—C13 | 118.23 (16) |
C2—C1—N1 | 123.56 (16) | C14—C15—C16 | 120.59 (16) |
C14—C1—N1 | 116.54 (15) | C14—C15—C4 | 120.00 (16) |
C3—C2—C1 | 120.80 (17) | C16—C15—C4 | 119.41 (15) |
C3—C2—H2 | 119.6 | C7—C16—C15 | 120.75 (16) |
C1—C2—H2 | 119.6 | C7—C16—C11 | 119.38 (16) |
C2—C3—C4 | 121.51 (17) | C15—C16—C11 | 119.85 (15) |
C2—C3—H3 | 119.2 | N1—C17—C18 | 120.16 (16) |
C4—C3—H3 | 119.2 | N1—C17—H17 | 119.9 |
C3—C4—C15 | 118.53 (15) | C18—C17—H17 | 119.9 |
C3—C4—C5 | 122.87 (16) | N2—C18—C19 | 122.82 (15) |
C15—C4—C5 | 118.58 (17) | N2—C18—C17 | 115.95 (15) |
C6—C5—C4 | 121.42 (17) | C19—C18—C17 | 121.22 (16) |
C6—C5—H5 | 119.3 | C20—C19—C18 | 119.85 (17) |
C4—C5—H5 | 119.3 | C20—C19—H19 | 120.1 |
C5—C6—C7 | 121.52 (17) | C18—C19—H19 | 120.1 |
C5—C6—H6 | 119.2 | C19—C20—C21 | 119.79 (16) |
C7—C6—H6 | 119.2 | C19—C20—H20 | 120.1 |
C8—C7—C16 | 119.11 (17) | C21—C20—H20 | 120.1 |
C8—C7—C6 | 122.58 (17) | C26—C21—C20 | 116.30 (15) |
C16—C7—C6 | 118.31 (17) | C26—C21—C22 | 118.96 (16) |
C9—C8—C7 | 120.85 (18) | C20—C21—C22 | 124.74 (16) |
C9—C8—H8 | 119.6 | C23—C22—C21 | 119.76 (17) |
C7—C8—H8 | 119.6 | C23—C22—H22 | 120.1 |
C8—C9—C10 | 120.73 (18) | C21—C22—H22 | 120.1 |
C8—C9—H9 | 119.6 | C22—C23—C24 | 121.80 (17) |
C10—C9—H9 | 119.6 | C22—C23—H23 | 119.1 |
C9—C10—C11 | 120.96 (18) | C24—C23—H23 | 119.1 |
C9—C10—H10 | 119.5 | C25—C24—C23 | 119.28 (18) |
C11—C10—H10 | 119.5 | C25—C24—H24 | 120.4 |
C10—C11—C16 | 118.96 (17) | C23—C24—H24 | 120.4 |
C10—C11—C12 | 123.13 (17) | O1—C25—C24 | 121.29 (17) |
C16—C11—C12 | 117.91 (16) | O1—C25—C26 | 118.13 (16) |
C13—C12—C11 | 122.10 (17) | C24—C25—C26 | 120.58 (17) |
C13—C12—H12 | 119.0 | N2—C26—C21 | 124.07 (16) |
C11—C12—H12 | 119.0 | N2—C26—C25 | 116.33 (15) |
C12—C13—C14 | 121.25 (16) | C21—C26—C25 | 119.60 (16) |
C12—C13—H13 | 119.4 | ||
C17—N1—C1—C2 | −26.9 (2) | C8—C7—C16—C11 | −0.1 (2) |
C17—N1—C1—C14 | 157.61 (16) | C6—C7—C16—C11 | −179.74 (15) |
C14—C1—C2—C3 | 0.8 (3) | C14—C15—C16—C7 | 177.43 (15) |
N1—C1—C2—C3 | −174.55 (16) | C4—C15—C16—C7 | −1.8 (2) |
C1—C2—C3—C4 | 0.4 (3) | C14—C15—C16—C11 | −1.1 (2) |
C2—C3—C4—C15 | −0.8 (2) | C4—C15—C16—C11 | 179.69 (14) |
C2—C3—C4—C5 | 177.58 (17) | C10—C11—C16—C7 | 0.0 (2) |
C3—C4—C5—C6 | −178.05 (18) | C12—C11—C16—C7 | −179.86 (15) |
C15—C4—C5—C6 | 0.4 (3) | C10—C11—C16—C15 | 178.57 (15) |
C4—C5—C6—C7 | −0.4 (3) | C12—C11—C16—C15 | −1.3 (2) |
C5—C6—C7—C8 | 179.80 (17) | C1—N1—C17—C18 | 174.56 (15) |
C5—C6—C7—C16 | −0.6 (3) | C26—N2—C18—C19 | −0.9 (2) |
C16—C7—C8—C9 | 0.0 (2) | C26—N2—C18—C17 | 177.84 (15) |
C6—C7—C8—C9 | 179.57 (17) | N1—C17—C18—N2 | 179.95 (16) |
C7—C8—C9—C10 | 0.3 (3) | N1—C17—C18—C19 | −1.3 (3) |
C8—C9—C10—C11 | −0.5 (3) | N2—C18—C19—C20 | 1.3 (3) |
C9—C10—C11—C16 | 0.3 (2) | C17—C18—C19—C20 | −177.40 (17) |
C9—C10—C11—C12 | −179.85 (17) | C18—C19—C20—C21 | −0.4 (3) |
C10—C11—C12—C13 | −177.25 (17) | C19—C20—C21—C26 | −0.8 (2) |
C16—C11—C12—C13 | 2.6 (2) | C19—C20—C21—C22 | 178.81 (18) |
C11—C12—C13—C14 | −1.5 (3) | C26—C21—C22—C23 | −0.2 (3) |
C2—C1—C14—C15 | −1.6 (2) | C20—C21—C22—C23 | −179.72 (18) |
N1—C1—C14—C15 | 174.06 (14) | C21—C22—C23—C24 | −0.7 (3) |
C2—C1—C14—C13 | 178.08 (15) | C22—C23—C24—C25 | 0.2 (3) |
N1—C1—C14—C13 | −6.2 (2) | C23—C24—C25—O1 | −177.90 (17) |
C12—C13—C14—C1 | 179.23 (16) | C23—C24—C25—C26 | 1.3 (3) |
C12—C13—C14—C15 | −1.0 (2) | C18—N2—C26—C21 | −0.4 (2) |
C1—C14—C15—C16 | −177.97 (15) | C18—N2—C26—C25 | 179.63 (15) |
C13—C14—C15—C16 | 2.3 (2) | C20—C21—C26—N2 | 1.2 (3) |
C1—C14—C15—C4 | 1.2 (2) | C22—C21—C26—N2 | −178.43 (16) |
C13—C14—C15—C4 | −178.51 (15) | C20—C21—C26—C25 | −178.82 (16) |
C3—C4—C15—C14 | 0.0 (2) | C22—C21—C26—C25 | 1.6 (2) |
C5—C4—C15—C14 | −178.49 (15) | O1—C25—C26—N2 | −2.9 (2) |
C3—C4—C15—C16 | 179.21 (15) | C24—C25—C26—N2 | 177.82 (17) |
C5—C4—C15—C16 | 0.7 (2) | O1—C25—C26—C21 | 177.05 (16) |
C8—C7—C16—C15 | −178.69 (15) | C24—C25—C26—C21 | −2.2 (3) |
C6—C7—C16—C15 | 1.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N2 | 0.91 (2) | 2.03 (2) | 2.666 (2) | 125 (2) |
C2—H2···O1i | 0.94 | 2.52 | 3.422 (2) | 161 |
C17—H17···O1i | 0.94 | 2.57 | 3.436 (2) | 153 |
Symmetry code: (i) −x, −y−1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N2 | 0.914 (16) | 2.03 (2) | 2.666 (2) | 125.0 (18) |
C2—H2···O1i | 0.94 | 2.52 | 3.422 (2) | 161 |
C17—H17···O1i | 0.94 | 2.57 | 3.436 (2) | 153 |
Symmetry code: (i) −x, −y−1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C26H16N2O |
Mr | 372.41 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 203 |
a, b, c (Å) | 15.9840 (19), 4.8453 (3), 23.071 (3) |
β (°) | 93.835 (9) |
V (Å3) | 1782.8 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.27 × 0.10 |
Data collection | |
Diffractometer | Stoe IPDS 2 |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17513, 3558, 2092 |
Rint | 0.075 |
(sin θ/λ)max (Å−1) | 0.623 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.093, 0.88 |
No. of reflections | 3558 |
No. of parameters | 265 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.12 |
Computer programs: X-AREA (Stoe & Cie, 2009), X-RED32 (Stoe & Cie, 2009), SHELXS2014 (Sheldrick, 2008), Mercury (Macrae et al., 2008), SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Acknowledgements
The University of Kalyani, and DST–FIST, DST–PURSE, New Delhi, are gratefully acknowledged for financial support, and instrumental and infrastructural facilities. HSE is grateful to the University of Neuchâtel for continued support.
References
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