organic compounds
Methyl 9-hydroxy-15-methyl-2-oxo-11-(pyren-1-yl)-10-oxa-15-azatetracyclo[7.6.0.01,12.03,8]pentadeca-3(8),4,6-triene-12-carboxylate
aDepartment of Physics, Presidency College, Chennai 600 005, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: aravindhanpresidency@gmail.com
In the title compound, C32H25NO5, the furan and pyrrole rings each adopt an the respective flap atoms being the C atom bearing the pyrene substituent and the CH2 atom adjacent to the N atom. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond. In the crystal, C—H⋯O contacts link the molecules, forming a two-dimensional network parallel to (001).
Related literature
For the solid–state structures of pyrenes, see: Robertson & White (1947); Camerman & Trotter (1965); Allmann (1970); Hazell et al. (1972); Kai et al. (1978). For a related structure, see: Gruber et al. (2010). For the use of pyrenes in fluorescence sensors, see: Bren (2001).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
10.1107/S1600536813024951/bt6925sup1.cif
contains datablocks I, 2R. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813024951/bt6925Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813024951/bt6925Isup3.cml
To a reaction mixture of 2-((3a2, 4-dihydropyren-1-yl)(hydroxy)methyl)acrylate (1 mmol), ninhydrine (1.1 mmol) and sarcosine (1.1 mmol) was refluxed in methanol until completion of the reaction was evidenced by TLC analysis. After completion of the reaction the solvent was evaporated under reduced pressure. The crude reaction mixture was dissolved in dichloromethane and washed with water followed by brine solution. The organic layer was separated and dried over sodium sulfate, filtering and evaporation of the organic solvent under reduced pressure. The product was separated by
using hexane and ethyl acetate (3:7) as an to give colorless solid. The product was dissolved in chloroform and heated for five minutes. The resulting solution was subjected to crystallization by slow evaporation of the solvent resulting in single crystals suitable for XRD studies.All the H atoms were positioned geometrically, with C–H = 0.93–0.97Å and constrained to ride on their parent atom, with Uiso(H) =1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. The hydroxyl H atom was freely refined.
Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).C32H25NO5 | F(000) = 2112 |
Mr = 503.53 | Dx = 1.356 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 8834 reflections |
a = 31.6964 (6) Å | θ = 2.1–31.2° |
b = 11.0325 (2) Å | µ = 0.09 mm−1 |
c = 14.1965 (3) Å | T = 293 K |
β = 96.503 (1)° | Block, colourless |
V = 4932.44 (17) Å3 | 0.25 × 0.20 × 0.20 mm |
Z = 8 |
Bruker Kappa APEXII CCD diffractometer | 4661 independent reflections |
Radiation source: fine-focus sealed tube | 3280 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω and ϕ scan | θmax = 25.7°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −38→37 |
Tmin = 0.979, Tmax = 0.983 | k = −11→13 |
20953 measured reflections | l = −17→17 |
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) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0547P)2 + 1.507P] where P = (Fo2 + 2Fc2)/3 |
4661 reflections | (Δ/σ)max < 0.001 |
347 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C32H25NO5 | V = 4932.44 (17) Å3 |
Mr = 503.53 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 31.6964 (6) Å | µ = 0.09 mm−1 |
b = 11.0325 (2) Å | T = 293 K |
c = 14.1965 (3) Å | 0.25 × 0.20 × 0.20 mm |
β = 96.503 (1)° |
Bruker Kappa APEXII CCD diffractometer | 4661 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 3280 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.983 | Rint = 0.031 |
20953 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.15 e Å−3 |
4661 reflections | Δρmin = −0.18 e Å−3 |
347 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.06963 (4) | 0.02788 (10) | 0.10712 (8) | 0.0468 (3) | |
O3 | 0.08806 (4) | 0.40608 (11) | −0.02173 (8) | 0.0555 (3) | |
O2 | 0.00524 (4) | 0.11622 (12) | 0.06940 (10) | 0.0499 (3) | |
N | 0.03715 (5) | 0.18310 (13) | −0.08500 (9) | 0.0468 (4) | |
C17 | 0.11197 (5) | 0.04084 (15) | 0.08207 (11) | 0.0396 (4) | |
H17 | 0.1286 | 0.0899 | 0.1304 | 0.048* | |
C16 | 0.13183 (5) | −0.08345 (15) | 0.07916 (11) | 0.0412 (4) | |
O4 | 0.16465 (4) | 0.24317 (13) | 0.03901 (10) | 0.0647 (4) | |
C1 | 0.23651 (5) | −0.24458 (17) | 0.12311 (11) | 0.0453 (4) | |
C2 | 0.19242 (5) | −0.22187 (16) | 0.09870 (11) | 0.0408 (4) | |
C3 | 0.17562 (5) | −0.10230 (15) | 0.10426 (10) | 0.0396 (4) | |
O5 | 0.15453 (5) | 0.19027 (15) | −0.11231 (10) | 0.0828 (5) | |
C23 | 0.05729 (5) | 0.23187 (15) | 0.16533 (11) | 0.0387 (4) | |
C25 | 0.07807 (5) | 0.32732 (16) | 0.03066 (11) | 0.0402 (4) | |
C10 | 0.25291 (6) | −0.36313 (19) | 0.11528 (12) | 0.0532 (5) | |
C13 | 0.16523 (6) | −0.31982 (16) | 0.06926 (12) | 0.0452 (4) | |
C15 | 0.10609 (6) | −0.18228 (16) | 0.05246 (13) | 0.0496 (5) | |
H15 | 0.0771 | −0.1702 | 0.0375 | 0.060* | |
C22 | 0.04826 (5) | 0.14005 (15) | 0.08771 (11) | 0.0396 (4) | |
C18 | 0.10582 (5) | 0.11345 (15) | −0.01307 (11) | 0.0391 (4) | |
C29 | 0.05082 (5) | 0.22207 (18) | 0.25959 (11) | 0.0484 (5) | |
H29 | 0.0407 | 0.1504 | 0.2832 | 0.058* | |
C24 | 0.07323 (5) | 0.33856 (16) | 0.13185 (11) | 0.0419 (4) | |
C14 | 0.12230 (6) | −0.29750 (16) | 0.04743 (13) | 0.0510 (5) | |
H14 | 0.1041 | −0.3614 | 0.0290 | 0.061* | |
C4 | 0.20465 (6) | −0.00815 (18) | 0.13747 (12) | 0.0491 (5) | |
H4 | 0.1947 | 0.0708 | 0.1417 | 0.059* | |
C5 | 0.24608 (6) | −0.0317 (2) | 0.16270 (13) | 0.0575 (5) | |
H5 | 0.2638 | 0.0315 | 0.1855 | 0.069* | |
C28 | 0.05960 (6) | 0.3202 (2) | 0.31740 (13) | 0.0608 (6) | |
H28 | 0.0545 | 0.3153 | 0.3805 | 0.073* | |
C21 | 0.08922 (6) | 0.03972 (17) | −0.10085 (12) | 0.0496 (5) | |
H21A | 0.1123 | 0.0165 | −0.1366 | 0.059* | |
H21B | 0.0747 | −0.0329 | −0.0831 | 0.059* | |
C6 | 0.26386 (6) | −0.1491 (2) | 0.15595 (13) | 0.0541 (5) | |
C20 | 0.05868 (6) | 0.12456 (18) | −0.15795 (12) | 0.0550 (5) | |
H20A | 0.0737 | 0.1832 | −0.1926 | 0.066* | |
H20B | 0.0388 | 0.0801 | −0.2022 | 0.066* | |
C26 | 0.08287 (6) | 0.43730 (18) | 0.19105 (13) | 0.0558 (5) | |
H26 | 0.0937 | 0.5085 | 0.1682 | 0.067* | |
C30 | 0.14512 (6) | 0.18882 (16) | −0.02412 (13) | 0.0461 (4) | |
C12 | 0.18277 (7) | −0.43904 (19) | 0.06394 (14) | 0.0593 (5) | |
H12 | 0.1650 | −0.5037 | 0.0452 | 0.071* | |
C11 | 0.22455 (7) | −0.4587 (2) | 0.08562 (14) | 0.0637 (6) | |
H11 | 0.2351 | −0.5368 | 0.0811 | 0.076* | |
C19 | 0.06708 (5) | 0.19699 (15) | 0.00068 (10) | 0.0375 (4) | |
C32 | 0.00976 (7) | 0.28537 (19) | −0.11593 (14) | 0.0617 (5) | |
H32A | −0.0029 | 0.3173 | −0.0628 | 0.092* | |
H32B | −0.0122 | 0.2587 | −0.1636 | 0.092* | |
H32C | 0.0263 | 0.3474 | −0.1418 | 0.092* | |
C9 | 0.29646 (7) | −0.3813 (2) | 0.13888 (15) | 0.0695 (6) | |
H9 | 0.3077 | −0.4585 | 0.1332 | 0.083* | |
C27 | 0.07588 (7) | 0.4264 (2) | 0.28456 (13) | 0.0642 (6) | |
H27 | 0.0821 | 0.4909 | 0.3259 | 0.077* | |
C7 | 0.30703 (7) | −0.1735 (3) | 0.17972 (16) | 0.0736 (7) | |
H7 | 0.3253 | −0.1114 | 0.2023 | 0.088* | |
C8 | 0.32282 (7) | −0.2884 (3) | 0.17003 (17) | 0.0783 (7) | |
H8 | 0.3517 | −0.3028 | 0.1848 | 0.094* | |
C31 | 0.18922 (11) | 0.2689 (3) | −0.1309 (2) | 0.1279 (13) | |
H31A | 0.1935 | 0.2635 | −0.1966 | 0.192* | |
H31B | 0.2147 | 0.2442 | −0.0925 | 0.192* | |
H31C | 0.1825 | 0.3510 | −0.1159 | 0.192* | |
H2 | 0.0041 (7) | 0.110 (2) | 0.0079 (16) | 0.081 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0466 (7) | 0.0380 (7) | 0.0591 (7) | 0.0011 (5) | 0.0194 (5) | 0.0090 (6) |
O3 | 0.0785 (9) | 0.0419 (7) | 0.0462 (7) | −0.0123 (7) | 0.0079 (6) | 0.0074 (6) |
O2 | 0.0402 (7) | 0.0526 (8) | 0.0577 (8) | −0.0076 (6) | 0.0101 (6) | −0.0048 (6) |
N | 0.0519 (9) | 0.0460 (9) | 0.0407 (7) | −0.0009 (7) | −0.0024 (6) | −0.0036 (7) |
C17 | 0.0378 (9) | 0.0375 (10) | 0.0445 (9) | −0.0044 (8) | 0.0080 (7) | 0.0011 (7) |
C16 | 0.0433 (10) | 0.0377 (10) | 0.0426 (9) | −0.0018 (8) | 0.0047 (7) | 0.0027 (7) |
O4 | 0.0629 (9) | 0.0629 (9) | 0.0671 (9) | −0.0265 (8) | 0.0021 (7) | 0.0046 (7) |
C1 | 0.0426 (11) | 0.0574 (12) | 0.0365 (8) | 0.0016 (9) | 0.0074 (7) | 0.0088 (8) |
C2 | 0.0437 (10) | 0.0452 (10) | 0.0337 (8) | 0.0001 (8) | 0.0060 (7) | 0.0025 (7) |
C3 | 0.0414 (10) | 0.0424 (10) | 0.0350 (8) | −0.0039 (8) | 0.0050 (7) | 0.0010 (7) |
O5 | 0.1044 (13) | 0.0818 (11) | 0.0715 (9) | −0.0397 (9) | 0.0505 (9) | −0.0140 (8) |
C23 | 0.0334 (9) | 0.0427 (10) | 0.0402 (9) | 0.0039 (8) | 0.0045 (7) | 0.0027 (7) |
C25 | 0.0447 (10) | 0.0365 (10) | 0.0392 (8) | −0.0012 (8) | 0.0035 (7) | 0.0026 (7) |
C10 | 0.0522 (12) | 0.0634 (13) | 0.0451 (10) | 0.0141 (10) | 0.0103 (8) | 0.0123 (9) |
C13 | 0.0527 (11) | 0.0380 (10) | 0.0440 (9) | 0.0029 (9) | 0.0013 (8) | 0.0020 (8) |
C15 | 0.0415 (10) | 0.0410 (11) | 0.0646 (11) | −0.0031 (9) | −0.0018 (8) | 0.0034 (9) |
C22 | 0.0370 (10) | 0.0358 (10) | 0.0468 (9) | −0.0008 (7) | 0.0085 (7) | 0.0041 (7) |
C18 | 0.0414 (10) | 0.0371 (10) | 0.0397 (8) | −0.0041 (8) | 0.0087 (7) | −0.0025 (7) |
C29 | 0.0442 (10) | 0.0612 (12) | 0.0399 (9) | 0.0072 (9) | 0.0046 (7) | 0.0085 (9) |
C24 | 0.0469 (10) | 0.0391 (10) | 0.0393 (8) | 0.0012 (8) | 0.0035 (7) | −0.0036 (8) |
C14 | 0.0511 (12) | 0.0347 (10) | 0.0642 (11) | −0.0068 (8) | −0.0061 (9) | 0.0029 (9) |
C4 | 0.0476 (11) | 0.0477 (11) | 0.0517 (10) | −0.0047 (9) | 0.0039 (8) | −0.0019 (8) |
C5 | 0.0487 (12) | 0.0633 (14) | 0.0594 (11) | −0.0167 (10) | 0.0009 (9) | 0.0015 (10) |
C28 | 0.0600 (13) | 0.0856 (16) | 0.0369 (9) | 0.0064 (12) | 0.0066 (8) | −0.0028 (10) |
C21 | 0.0592 (12) | 0.0443 (11) | 0.0462 (9) | −0.0039 (9) | 0.0103 (8) | −0.0077 (8) |
C6 | 0.0433 (11) | 0.0684 (14) | 0.0510 (10) | −0.0006 (10) | 0.0075 (8) | 0.0128 (10) |
C20 | 0.0718 (13) | 0.0519 (12) | 0.0400 (9) | −0.0019 (10) | 0.0009 (9) | −0.0079 (8) |
C26 | 0.0668 (13) | 0.0486 (12) | 0.0515 (11) | −0.0036 (10) | 0.0039 (9) | −0.0078 (9) |
C30 | 0.0496 (11) | 0.0405 (10) | 0.0505 (10) | −0.0034 (9) | 0.0153 (9) | 0.0007 (8) |
C12 | 0.0681 (14) | 0.0445 (12) | 0.0634 (12) | 0.0053 (10) | −0.0009 (10) | −0.0007 (9) |
C11 | 0.0729 (15) | 0.0534 (13) | 0.0647 (12) | 0.0182 (12) | 0.0071 (11) | 0.0018 (10) |
C19 | 0.0424 (10) | 0.0343 (9) | 0.0358 (8) | −0.0038 (7) | 0.0040 (7) | −0.0005 (7) |
C32 | 0.0629 (13) | 0.0666 (14) | 0.0523 (11) | 0.0053 (11) | −0.0078 (9) | −0.0007 (10) |
C9 | 0.0585 (14) | 0.0812 (17) | 0.0708 (13) | 0.0222 (13) | 0.0164 (11) | 0.0211 (12) |
C27 | 0.0731 (14) | 0.0703 (15) | 0.0484 (11) | 0.0027 (12) | 0.0027 (10) | −0.0226 (10) |
C7 | 0.0442 (13) | 0.0909 (19) | 0.0843 (15) | −0.0056 (12) | 0.0016 (11) | 0.0195 (13) |
C8 | 0.0431 (13) | 0.103 (2) | 0.0890 (16) | 0.0141 (14) | 0.0087 (11) | 0.0327 (15) |
C31 | 0.152 (3) | 0.123 (3) | 0.126 (2) | −0.074 (2) | 0.091 (2) | −0.015 (2) |
O1—C22 | 1.423 (2) | C18—C21 | 1.531 (2) |
O1—C17 | 1.4340 (18) | C18—C19 | 1.565 (2) |
O3—C25 | 1.2090 (19) | C29—C28 | 1.368 (3) |
O2—C22 | 1.384 (2) | C29—H29 | 0.9300 |
O2—H2 | 0.87 (2) | C24—C26 | 1.389 (2) |
N—C20 | 1.455 (2) | C14—H14 | 0.9300 |
N—C32 | 1.460 (2) | C4—C5 | 1.347 (3) |
N—C19 | 1.464 (2) | C4—H4 | 0.9300 |
C17—C16 | 1.511 (2) | C5—C6 | 1.420 (3) |
C17—C18 | 1.563 (2) | C5—H5 | 0.9300 |
C17—H17 | 0.9800 | C28—C27 | 1.382 (3) |
C16—C15 | 1.389 (2) | C28—H28 | 0.9300 |
C16—C3 | 1.409 (2) | C21—C20 | 1.514 (3) |
O4—C30 | 1.192 (2) | C21—H21A | 0.9700 |
C1—C6 | 1.410 (3) | C21—H21B | 0.9700 |
C1—C10 | 1.416 (3) | C6—C7 | 1.398 (3) |
C1—C2 | 1.423 (2) | C20—H20A | 0.9700 |
C2—C13 | 1.415 (2) | C20—H20B | 0.9700 |
C2—C3 | 1.428 (2) | C26—C27 | 1.376 (3) |
C3—C4 | 1.432 (2) | C26—H26 | 0.9300 |
O5—C30 | 1.319 (2) | C12—C11 | 1.343 (3) |
O5—C31 | 1.448 (3) | C12—H12 | 0.9300 |
C23—C29 | 1.381 (2) | C11—H11 | 0.9300 |
C23—C24 | 1.386 (2) | C32—H32A | 0.9600 |
C23—C22 | 1.500 (2) | C32—H32B | 0.9600 |
C25—C24 | 1.467 (2) | C32—H32C | 0.9600 |
C25—C19 | 1.529 (2) | C9—C8 | 1.364 (3) |
C10—C9 | 1.398 (3) | C9—H9 | 0.9300 |
C10—C11 | 1.418 (3) | C27—H27 | 0.9300 |
C13—C14 | 1.383 (2) | C7—C8 | 1.375 (3) |
C13—C12 | 1.433 (3) | C7—H7 | 0.9300 |
C15—C14 | 1.376 (3) | C8—H8 | 0.9300 |
C15—H15 | 0.9300 | C31—H31A | 0.9600 |
C22—C19 | 1.563 (2) | C31—H31B | 0.9600 |
C18—C30 | 1.521 (2) | C31—H31C | 0.9600 |
C22—O1—C17 | 107.67 (12) | C4—C5—C6 | 122.74 (19) |
C22—O2—H2 | 97.4 (15) | C4—C5—H5 | 118.6 |
C20—N—C32 | 116.09 (14) | C6—C5—H5 | 118.6 |
C20—N—C19 | 109.02 (14) | C29—C28—C27 | 121.79 (17) |
C32—N—C19 | 118.45 (14) | C29—C28—H28 | 119.1 |
O1—C17—C16 | 108.71 (13) | C27—C28—H28 | 119.1 |
O1—C17—C18 | 103.69 (12) | C20—C21—C18 | 104.32 (14) |
C16—C17—C18 | 116.93 (13) | C20—C21—H21A | 110.9 |
O1—C17—H17 | 109.1 | C18—C21—H21A | 110.9 |
C16—C17—H17 | 109.1 | C20—C21—H21B | 110.9 |
C18—C17—H17 | 109.1 | C18—C21—H21B | 110.9 |
C15—C16—C3 | 118.99 (16) | H21A—C21—H21B | 108.9 |
C15—C16—C17 | 119.09 (15) | C7—C6—C1 | 119.0 (2) |
C3—C16—C17 | 121.91 (15) | C7—C6—C5 | 123.0 (2) |
C6—C1—C10 | 119.89 (17) | C1—C6—C5 | 118.03 (17) |
C6—C1—C2 | 119.93 (17) | N—C20—C21 | 102.50 (13) |
C10—C1—C2 | 120.17 (17) | N—C20—H20A | 111.3 |
C13—C2—C1 | 119.05 (16) | C21—C20—H20A | 111.3 |
C13—C2—C3 | 120.21 (15) | N—C20—H20B | 111.3 |
C1—C2—C3 | 120.74 (16) | C21—C20—H20B | 111.3 |
C16—C3—C2 | 119.03 (15) | H20A—C20—H20B | 109.2 |
C16—C3—C4 | 123.66 (16) | C27—C26—C24 | 117.84 (19) |
C2—C3—C4 | 117.30 (15) | C27—C26—H26 | 121.1 |
C30—O5—C31 | 115.97 (18) | C24—C26—H26 | 121.1 |
C29—C23—C24 | 119.91 (16) | O4—C30—O5 | 123.62 (17) |
C29—C23—C22 | 128.47 (16) | O4—C30—C18 | 124.01 (15) |
C24—C23—C22 | 111.60 (13) | O5—C30—C18 | 112.35 (16) |
O3—C25—C24 | 127.25 (16) | C11—C12—C13 | 120.96 (19) |
O3—C25—C19 | 124.89 (14) | C11—C12—H12 | 119.5 |
C24—C25—C19 | 107.84 (13) | C13—C12—H12 | 119.5 |
C9—C10—C1 | 118.4 (2) | C12—C11—C10 | 121.56 (19) |
C9—C10—C11 | 122.7 (2) | C12—C11—H11 | 119.2 |
C1—C10—C11 | 118.93 (17) | C10—C11—H11 | 119.2 |
C14—C13—C2 | 118.74 (16) | N—C19—C25 | 115.83 (13) |
C14—C13—C12 | 121.95 (17) | N—C19—C22 | 110.19 (13) |
C2—C13—C12 | 119.31 (17) | C25—C19—C22 | 104.67 (12) |
C14—C15—C16 | 121.89 (17) | N—C19—C18 | 106.18 (12) |
C14—C15—H15 | 119.1 | C25—C19—C18 | 115.56 (13) |
C16—C15—H15 | 119.1 | C22—C19—C18 | 103.71 (12) |
O2—C22—O1 | 107.96 (13) | N—C32—H32A | 109.5 |
O2—C22—C23 | 111.60 (13) | N—C32—H32B | 109.5 |
O1—C22—C23 | 113.46 (13) | H32A—C32—H32B | 109.5 |
O2—C22—C19 | 112.58 (13) | N—C32—H32C | 109.5 |
O1—C22—C19 | 106.66 (12) | H32A—C32—H32C | 109.5 |
C23—C22—C19 | 104.54 (13) | H32B—C32—H32C | 109.5 |
C30—C18—C21 | 114.63 (14) | C8—C9—C10 | 121.4 (2) |
C30—C18—C17 | 110.23 (13) | C8—C9—H9 | 119.3 |
C21—C18—C17 | 115.39 (14) | C10—C9—H9 | 119.3 |
C30—C18—C19 | 110.75 (13) | C26—C27—C28 | 120.44 (18) |
C21—C18—C19 | 102.26 (13) | C26—C27—H27 | 119.8 |
C17—C18—C19 | 102.52 (12) | C28—C27—H27 | 119.8 |
C28—C29—C23 | 118.49 (18) | C8—C7—C6 | 120.7 (2) |
C28—C29—H29 | 120.8 | C8—C7—H7 | 119.6 |
C23—C29—H29 | 120.8 | C6—C7—H7 | 119.6 |
C23—C24—C26 | 121.50 (15) | C9—C8—C7 | 120.6 (2) |
C23—C24—C25 | 110.28 (15) | C9—C8—H8 | 119.7 |
C26—C24—C25 | 128.21 (16) | C7—C8—H8 | 119.7 |
C15—C14—C13 | 121.10 (17) | O5—C31—H31A | 109.5 |
C15—C14—H14 | 119.5 | O5—C31—H31B | 109.5 |
C13—C14—H14 | 119.5 | H31A—C31—H31B | 109.5 |
C5—C4—C3 | 121.22 (18) | O5—C31—H31C | 109.5 |
C5—C4—H4 | 119.4 | H31A—C31—H31C | 109.5 |
C3—C4—H4 | 119.4 | H31B—C31—H31C | 109.5 |
C22—O1—C17—C16 | −166.42 (13) | C10—C1—C6—C7 | 0.4 (3) |
C22—O1—C17—C18 | −41.34 (15) | C2—C1—C6—C7 | 179.86 (16) |
O1—C17—C16—C15 | 31.7 (2) | C10—C1—C6—C5 | 180.00 (16) |
C18—C17—C16—C15 | −85.17 (19) | C2—C1—C6—C5 | −0.6 (2) |
O1—C17—C16—C3 | −147.21 (14) | C4—C5—C6—C7 | 178.29 (18) |
C18—C17—C16—C3 | 95.89 (18) | C4—C5—C6—C1 | −1.3 (3) |
C6—C1—C2—C13 | −177.65 (15) | C32—N—C20—C21 | 170.80 (15) |
C10—C1—C2—C13 | 1.8 (2) | C19—N—C20—C21 | 33.93 (18) |
C6—C1—C2—C3 | 2.0 (2) | C18—C21—C20—N | −40.11 (18) |
C10—C1—C2—C3 | −178.61 (14) | C23—C24—C26—C27 | −0.4 (3) |
C15—C16—C3—C2 | 1.9 (2) | C25—C24—C26—C27 | −179.51 (18) |
C17—C16—C3—C2 | −179.16 (14) | C31—O5—C30—O4 | −3.6 (3) |
C15—C16—C3—C4 | −176.69 (16) | C31—O5—C30—C18 | 174.6 (2) |
C17—C16—C3—C4 | 2.3 (2) | C21—C18—C30—O4 | −173.00 (18) |
C13—C2—C3—C16 | −0.6 (2) | C17—C18—C30—O4 | −40.8 (2) |
C1—C2—C3—C16 | 179.76 (14) | C19—C18—C30—O4 | 71.9 (2) |
C13—C2—C3—C4 | 178.05 (14) | C21—C18—C30—O5 | 8.9 (2) |
C1—C2—C3—C4 | −1.6 (2) | C17—C18—C30—O5 | 141.05 (16) |
C6—C1—C10—C9 | −1.3 (2) | C19—C18—C30—O5 | −106.19 (17) |
C2—C1—C10—C9 | 179.25 (15) | C14—C13—C12—C11 | −179.88 (18) |
C6—C1—C10—C11 | 177.55 (16) | C2—C13—C12—C11 | −0.6 (3) |
C2—C1—C10—C11 | −1.9 (2) | C13—C12—C11—C10 | 0.5 (3) |
C1—C2—C13—C14 | 178.75 (15) | C9—C10—C11—C12 | 179.54 (18) |
C3—C2—C13—C14 | −0.9 (2) | C1—C10—C11—C12 | 0.7 (3) |
C1—C2—C13—C12 | −0.5 (2) | C20—N—C19—C25 | 115.29 (16) |
C3—C2—C13—C12 | 179.85 (15) | C32—N—C19—C25 | −20.4 (2) |
C3—C16—C15—C14 | −1.7 (3) | C20—N—C19—C22 | −126.17 (15) |
C17—C16—C15—C14 | 179.29 (16) | C32—N—C19—C22 | 98.12 (17) |
C17—O1—C22—O2 | 153.13 (13) | C20—N—C19—C18 | −14.48 (17) |
C17—O1—C22—C23 | −82.64 (15) | C32—N—C19—C18 | −150.18 (15) |
C17—O1—C22—C19 | 31.92 (16) | O3—C25—C19—N | −47.9 (2) |
C29—C23—C22—O2 | 64.5 (2) | C24—C25—C19—N | 130.74 (15) |
C24—C23—C22—O2 | −113.96 (16) | O3—C25—C19—C22 | −169.45 (16) |
C29—C23—C22—O1 | −57.7 (2) | C24—C25—C19—C22 | 9.20 (17) |
C24—C23—C22—O1 | 123.81 (15) | O3—C25—C19—C18 | 77.2 (2) |
C29—C23—C22—C19 | −173.51 (16) | C24—C25—C19—C18 | −104.17 (15) |
C24—C23—C22—C19 | 8.00 (18) | O2—C22—C19—N | −14.03 (19) |
O1—C17—C18—C30 | 151.21 (13) | O1—C22—C19—N | 104.20 (15) |
C16—C17—C18—C30 | −89.18 (17) | C23—C22—C19—N | −135.34 (14) |
O1—C17—C18—C21 | −76.99 (16) | O2—C22—C19—C25 | 111.15 (15) |
C16—C17—C18—C21 | 42.6 (2) | O1—C22—C19—C25 | −130.62 (13) |
O1—C17—C18—C19 | 33.26 (15) | C23—C22—C19—C25 | −10.16 (16) |
C16—C17—C18—C19 | 152.87 (14) | O2—C22—C19—C18 | −127.32 (14) |
C24—C23—C29—C28 | 1.4 (3) | O1—C22—C19—C18 | −9.09 (16) |
C22—C23—C29—C28 | −176.98 (17) | C23—C22—C19—C18 | 111.37 (13) |
C29—C23—C24—C26 | −0.2 (3) | C30—C18—C19—N | 111.87 (15) |
C22—C23—C24—C26 | 178.41 (16) | C21—C18—C19—N | −10.71 (16) |
C29—C23—C24—C25 | 179.07 (15) | C17—C18—C19—N | −130.55 (13) |
C22—C23—C24—C25 | −2.3 (2) | C30—C18—C19—C25 | −18.05 (18) |
O3—C25—C24—C23 | 173.97 (17) | C21—C18—C19—C25 | −140.62 (14) |
C19—C25—C24—C23 | −4.64 (19) | C17—C18—C19—C25 | 99.53 (14) |
O3—C25—C24—C26 | −6.8 (3) | C30—C18—C19—C22 | −131.98 (14) |
C19—C25—C24—C26 | 174.59 (18) | C21—C18—C19—C22 | 105.45 (14) |
C16—C15—C14—C13 | 0.2 (3) | C17—C18—C19—C22 | −14.40 (15) |
C2—C13—C14—C15 | 1.1 (3) | C1—C10—C9—C8 | 0.9 (3) |
C12—C13—C14—C15 | −179.64 (17) | C11—C10—C9—C8 | −177.93 (19) |
C16—C3—C4—C5 | 178.38 (16) | C24—C26—C27—C28 | −0.3 (3) |
C2—C3—C4—C5 | −0.2 (2) | C29—C28—C27—C26 | 1.5 (3) |
C3—C4—C5—C6 | 1.7 (3) | C1—C6—C7—C8 | 0.9 (3) |
C23—C29—C28—C27 | −2.0 (3) | C5—C6—C7—C8 | −178.6 (2) |
C30—C18—C21—C20 | −89.05 (18) | C10—C9—C8—C7 | 0.5 (3) |
C17—C18—C21—C20 | 141.26 (15) | C6—C7—C8—C9 | −1.4 (3) |
C19—C18—C21—C20 | 30.85 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C27—H27···O3i | 0.93 | 2.43 | 3.299 (2) | 155 |
O2—H2···N | 0.87 (2) | 1.95 (2) | 2.6217 (19) | 133 (2) |
Symmetry code: (i) x, −y+1, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C27—H27···O3i | 0.93 | 2.43 | 3.299 (2) | 155.4 |
O2—H2···N | 0.87 (2) | 1.95 (2) | 2.6217 (19) | 133 (2) |
Symmetry code: (i) x, −y+1, z+1/2. |
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Owing to their electronic, optical and geometric properties, mono-functionalized pyrenes, attachable to a receptor platform, are of special interest for the development of fluorescent sensors (Bren et al., 2001).
The pyrene moiety alone shows no significant deviations of bond lengths and angles compared with those of the unsubstituted analogue (Robertson et al., 1947; Camerman et al., 1965; Allmann et al., 1970; Hazell et al., 1972; Kai et al., 1978). The furan and pyrole rings adopt an envelope conformation. C17 and C20 are displaced by -0.2843 (2) Å and 0.2851 (2) Å, respectively, from the least-square planes formed by the remaining ring atoms. The dihedral angle between the furan and pyrole ring being 65.50 (6)°. The carboxylate group (C30/05/C31) is almost perpendicular to the furan ring with dihedral angle of 85.05 (1)°. The molecular conformation is stabilized by an intramolecular O—H···N hydrogen bond and the crystal packing is stabilized by intermolecular C—H···O contacts.