Acta Crystallographica Section E: Crystallographic Communications

Acta Crystallogr E Crystallogr Commun. 72(Pt 12): 1731-1733

Crystal structure of 1,3-bis[(E)-4-methoxybenzylideneamino]propan-2-ol

Augusto Riveraa*, Ingrid Miranda-Carvajala, Jaime Ríos-Mottaa, Michael Bolteb

a. Universidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No. 45-03, Bogotá, Código Postal 111321, Colombia

b. Institut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von Laue-Strasse 7, 60438 Frankfurt/Main, Germany

Correspondence e-mail: ariverau@unal.edu.co

© Rivera et al. 2016

DOI: 10.1107/S2056989016016947

Published online: 04 November 2016

Abstract

In the crystal of 1,3-bis[(E)-4-methoxybenzylideneamino]propan-2-ol, molecules are linked by O—H⋯N hydrogen bonds into C(5) supramolecular chains propagating along the a-axis direction.

Abstract

The title Schiff base, C₁₉H₂₂N₂O₃, was synthesized via the condensation reaction of 1,3-diaminopropan-2-ol with 4-methoxybenzaldehyde using water as solvent. The molecule exists in an E,E conformation with respect to the C=N imine bonds and the dihedral angle between the aromatic rings is 37.25 (15)°. In the crystal, O—H⋯N hydrogen bonds link the molecules into infinite C(5) chains propagating along the a-axis direction. The packing of these chains is consolidated by C—H⋯O interactions and C—H⋯π short contacts, forming a three-dimensional network.

Chemical context  

Compounds containing the –C=N– (azomethine group) structure are known as Schiff bases, usually synthesized from the condensation of primary amines and active carbonyl groups (Bekdemir & Efil, 2014 ▸). Imines are one class of the most important and fundamental unsaturated organic compounds with a C=N double bond as their characteristic chemical bond and are extensively present in natural products and many drugs (Zhu et al., 2010 ▸). The formation of imines underlies a discipline known as dynamic covalent chemistry (DCC), which is now used widely in the construction of exotic molecules and extended structures such as rotaxanes, catenanes, and so on (Patil & Adimurthy, 2013 ▸). Schiff base compounds derived from 1,n-diamines play an important role in coordination chemistry and have been studied extensively for their broad range of biological activities (Sahu et al. 2012 ▸; da Silva et al., 2011 ▸; Przybylski et al. 2009 ▸; Dhar & Taploo, 1982 ▸). The common structural feature of these compounds is the presence of two azomethine groups linked by an n-methylene bridge, which can act as hydrogen-bond acceptors.

The title compound is interesting in that the presence of an OH group in the 1,3-diamine molecule is situated in a favorable position towards the azomethine groups to form an intramolecular hydrogen bond. Thus, one may expect that the charge distribution around the azomethine nitrogen atoms may be visibly perturbed by the presence of this type of interaction. Hence, 1,3-diaminepropan-2ol was chosen with the expectation that the presence of an OH group would result in an intramolecular hydrogen bond. The title compound was synthesized quickly and efficiently by condensation of 1,3-diamine-2-propanol and p-methoxybenzaldehyde using a simple water-mediated procedure that requires neither a catalyst nor any additive (Rivera, et al., 2016 ▸). To the best of our knowledge, no X-ray crystal structure of either the uncoordinated or the coordinated title compound has been reported previously.

Structural commentary  

The molecular structure of the title compound is illustrated in Fig. 1 ▸. The title compound exists in an E,E conformation with respect to the N1=C1 and N2=C5 azomethine bonds and the C2—N1=C1—C11 and C4—N2=C5—C21 torsion angles are 175.6 (3) and −178.3 (3)° respectively. The N1=C1 and N2=C5 distances of 1.265 (4) and 1.271 (4) Å, respectively, are consistent with C=N double bonding. The bond angles of 117.0 (3) and 117.7 (3)° around the N1 and N2 atoms confirm their sp ² character. The slight differences between N=C distances and C—N=C angles are due to the significant effect of the hydrogen bond on the geometric parameters of the nitrogen atom (N2) involved in the intermolecular hydrogen bond (see below).

The N1—C2—C3—C4 torsion angle is −64.4 (4)° and the C2—C3—C4—N2 torsion angle is 175.0 (3)°. The O1—C3—C4—N2 torsion angle is −65.3 (3)°, which has a significant role to play in the hydrogen-bonding pattern in the crystal of the title compound (see below). The two methoxy substituents are essentially coplanar with their bound benzene rings with torsion angles C17—O2—C14—C13 = 169.3 (3)° and C27—O3—C24—C23 = −172.2 (3)°.

Supramolecular features  

Rather than the proposed intramolecular O—H⋯N hydrogen bond, adjacent molecules in the crystal of the title compound are linked by intermolecular O—H⋯N hydrogen bonds (Table 1 ▸, Fig. 2 ▸), forming an infinite zigzag C(5) chains extending along the a-axis direction. The chains are further linked to neighbouring chains through a pair of weak C—H⋯O hydrogen bonds (Table 1 ▸). Furthermore, C12—H12 and C22—H22 form weaker C—H⋯Cg (π–ring) interactions (Table 1 ▸), which connect the chains of consecutive layers, thus forming a three-dimensional supramolecular network (Fig. 2 ▸).

Database survey  

No comparable structure of either the uncoordinated or the coordinated title compound has been found in the Cambridge Crystallographic Database.

Synthesis and crystallization  

The title compound was prepared according to our published method (Rivera et al., 2016 ▸). The crude product was dissolved in benzene and acetonitrile was added to the solution: upon slow evaporation of the solvent, colorless plates of the title compound arose. M.p. 403 K, yield 88%.

Refinement  

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The hydroxyl H atom was refined freely; however, the remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with d(C—H) = 0.95 Å for aromatic and azomethine atoms, d(C—H) = 0.99 Å for methylene, d(C—H) = 1.00 Å for C3—H3 and 0.98 Å for CH₃ atoms. The U iso values were constrained to be 1.5U eq of the carrier atom for methyl H atoms and 1.2U eq for the remaining H atoms. A rotating group model was used for the methyl groups. The absolute structure of the crystal chosen for data collection was indeterminate in the present refinement.

Figure 1View larger versionFigure 1. The molecular structure of the title compound, Displacement ellipsoids are drawn at the 50% probability level.

Figure 2View larger versionFigure 2. Partial packing diagram of the title compound, showing an extended hydrogen-bonded network. H atoms not involved in hydrogen bonds have been omitted for clarity.

See full tableTable 1. Hydrogen-bond geometry (Å, °) Cg1 and Cg2 are the centroids of the C11–C16 and C21–C26 rings, respectively.

See full table Table 2. Experimental details

Supplementary Material

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Acknowledgments

We acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia for financial support of this work (research project No. 28427). IMC is also grateful to COLCIENCIAS for her doctoral scholarship

supplementary crystallographic information

Crystal data

See full table

Data collection

See full table

Refinement

See full table

Special details

See full table

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

See full table

Atomic displacement parameters (Å²)

See full table

Geometric parameters (Å, º)

See full table

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the C11–C16 and C21–C26 rings, respectively.

See full table

Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) −x, −y+1, z−1/2; (iii) −x, −y+1, z+1/2; (iv) −x+1/2, y+3/2, z+1/2.

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References

Bekdemir, Y. & Efil, K. (2014). Org. Chem. Int. article ID 816487.

Dhar, D. N. & Taploo, C. L. (1982). J. Sci. Ind. Res. 41, 501–506.

Patil, R. D. & Adimurthy, S. (2013). Asia. J. Org. Chem. 2, 726–744.

Przybylski, P., Huczyński, A., Pyta, K., Brzezinski, B. & Bartl, F. (2009). Curr. Org. Chem. 13, 124–148.

Rivera, A., Miranda-Carvajal, I. & Ríos-Motta, J. (2016). Int. J. Chem. 8, 62–68.

Sahu, R., Thakur, D. S. & Kashyap, P. (2012). Int. J. Pharm. Sci. Nanotech. 5, 1757–1764.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.

Silva, C. M. da, da Silva, D. L., Modolo, L. V., Alves, R. B., de Resende, M. A., Martins, C. V. B., de Fátima, Â. & Ângelo, (2011). J. Adv. Res. 2, 1–8.

Stoe & Cie (2001). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.

Zhu, X.-Q., Liu, Q.-Y., Chen, Q. & Mei, L.-R. (2010). J. Org. Chem. 75, 789–808.

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C₁₉H₂₂N₂O₃ | Dx = 1.253 Mg m⁻³
Mr = 326.38 | Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁ | Cell parameters from 12316 reflections
a = 7.9081 (3) Å | θ = 2.2–26.0°
b = 5.8434 (3) Å | µ = 0.09 mm⁻¹
c = 37.4435 (16) Å | T = 173 K
V = 1730.27 (13) Å³ | Plate, colourless
Z = 4 | 0.28 × 0.19 × 0.08 mm
F(000) = 696 |

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Stoe IPDS II two-circle diffractometer | 2786 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.038
ω scans | θmax = 25.6°, θmin = 2.2°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −9→9
Tmin = 0.625, Tmax = 1.000 | k = −7→7
12316 measured reflections | l = −41→45
3084 independent reflections |

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Refinement on F² | Hydrogen site location: mixed
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.046 | w = 1/[σ²(Fo²) + (0.0961P)²] where P = (Fo² + 2Fc²)/3
wR(F²) = 0.123 | (Δ/σ)max < 0.001
S = 1.01 | Δρmax = 0.15 e Å⁻³
3084 reflections | Δρmin = −0.16 e Å⁻³
224 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc²λ³/sin(2θ)]-1/4
1 restraint | Extinction coefficient: 0.046 (8)

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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.

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| x | y | z | Uiso*/Ueq |
N1 | 0.5510 (4) | 0.4188 (4) | 0.44173 (8) | 0.0467 (6) |
N2 | 0.3474 (4) | 0.4764 (4) | 0.54792 (8) | 0.0453 (6) |
O1 | 0.7066 (3) | 0.4483 (4) | 0.53519 (7) | 0.0513 (6) |
H1 | 0.754 (7) | 0.302 (9) | 0.5410 (13) | 0.073 (13)* |
O2 | 0.1888 (4) | 0.4687 (4) | 0.28786 (6) | 0.0547 (6) |
O3 | 0.0967 (3) | 0.4509 (4) | 0.71286 (7) | 0.0542 (6) |
C1 | 0.5258 (4) | 0.5772 (6) | 0.41931 (9) | 0.0463 (7) |
H1A | 0.5738 | 0.7234 | 0.4238 | 0.056* |
C2 | 0.6638 (5) | 0.4706 (6) | 0.47176 (9) | 0.0518 (8) |
H2A | 0.6906 | 0.6361 | 0.4716 | 0.062* |
H2B | 0.7711 | 0.3856 | 0.4687 | 0.062* |
C3 | 0.5858 (4) | 0.4072 (5) | 0.50766 (9) | 0.0461 (7) |
H3 | 0.5540 | 0.2416 | 0.5076 | 0.055* |
C4 | 0.4306 (4) | 0.5507 (5) | 0.51505 (9) | 0.0491 (8) |
H4A | 0.4637 | 0.7134 | 0.5173 | 0.059* |
H4B | 0.3507 | 0.5371 | 0.4948 | 0.059* |
C5 | 0.3529 (4) | 0.6102 (5) | 0.57466 (9) | 0.0448 (7) |
H5 | 0.4082 | 0.7533 | 0.5717 | 0.054* |
C11 | 0.4253 (4) | 0.5452 (5) | 0.38653 (9) | 0.0414 (7) |
C12 | 0.4251 (5) | 0.7189 (5) | 0.36069 (10) | 0.0477 (7) |
H12 | 0.4806 | 0.8597 | 0.3655 | 0.057* |
C13 | 0.3447 (4) | 0.6874 (6) | 0.32820 (9) | 0.0484 (8) |
H13 | 0.3464 | 0.8057 | 0.3108 | 0.058* |
C14 | 0.2617 (4) | 0.4832 (5) | 0.32098 (9) | 0.0442 (7) |
C15 | 0.2578 (4) | 0.3105 (5) | 0.34676 (9) | 0.0436 (7) |
H15 | 0.1994 | 0.1716 | 0.3421 | 0.052* |
C16 | 0.3392 (4) | 0.3430 (5) | 0.37899 (8) | 0.0437 (7) |
H16 | 0.3365 | 0.2247 | 0.3964 | 0.052* |
C17 | 0.1278 (5) | 0.2506 (6) | 0.27655 (10) | 0.0553 (8) |
H17A | 0.2219 | 0.1415 | 0.2758 | 0.083* |
H17B | 0.0778 | 0.2645 | 0.2527 | 0.083* |
H17C | 0.0420 | 0.1961 | 0.2934 | 0.083* |
C21 | 0.2798 (4) | 0.5588 (5) | 0.60975 (9) | 0.0435 (7) |
C22 | 0.3029 (4) | 0.7163 (5) | 0.63743 (9) | 0.0472 (7) |
H22 | 0.3628 | 0.8540 | 0.6328 | 0.057* |
C23 | 0.2409 (5) | 0.6766 (5) | 0.67121 (9) | 0.0499 (8) |
H23 | 0.2581 | 0.7865 | 0.6896 | 0.060* |
C24 | 0.1526 (4) | 0.4751 (5) | 0.67851 (9) | 0.0445 (7) |
C25 | 0.1277 (4) | 0.3152 (5) | 0.65135 (9) | 0.0445 (7) |
H25 | 0.0677 | 0.1776 | 0.6561 | 0.053* |
C26 | 0.1910 (4) | 0.3579 (5) | 0.61733 (9) | 0.0455 (7) |
H26 | 0.1734 | 0.2485 | 0.5989 | 0.055* |
C27 | 0.0252 (5) | 0.2384 (6) | 0.72315 (10) | 0.0582 (9) |
H27A | −0.0747 | 0.2069 | 0.7085 | 0.087* |
H27B | −0.0079 | 0.2450 | 0.7484 | 0.087* |
H27C | 0.1086 | 0.1163 | 0.7197 | 0.087* |

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| U ¹¹ | U ²² | U ³³ | U ¹² | U ¹³ | U ²³
N1 | 0.0514 (14) | 0.0482 (13) | 0.0404 (13) | −0.0007 (12) | 0.0008 (12) | −0.0031 (12)
N2 | 0.0506 (15) | 0.0425 (13) | 0.0429 (14) | 0.0044 (11) | −0.0030 (12) | −0.0012 (11)
O1 | 0.0585 (14) | 0.0457 (12) | 0.0498 (13) | 0.0004 (11) | −0.0133 (11) | −0.0031 (10)
O2 | 0.0675 (16) | 0.0507 (13) | 0.0459 (14) | 0.0031 (11) | −0.0074 (11) | 0.0050 (10)
O3 | 0.0623 (15) | 0.0522 (13) | 0.0479 (13) | −0.0001 (11) | 0.0034 (12) | −0.0082 (10)
C1 | 0.0470 (17) | 0.0461 (16) | 0.0459 (18) | −0.0049 (14) | 0.0055 (14) | −0.0027 (13)
C2 | 0.0499 (18) | 0.056 (2) | 0.049 (2) | −0.0019 (14) | −0.0035 (15) | −0.0018 (14)
C3 | 0.0507 (17) | 0.0425 (15) | 0.0451 (17) | −0.0028 (13) | −0.0076 (14) | −0.0013 (13)
C4 | 0.0588 (18) | 0.0434 (16) | 0.0451 (18) | 0.0032 (14) | −0.0021 (14) | 0.0040 (14)
C5 | 0.0472 (17) | 0.0373 (15) | 0.0501 (18) | 0.0021 (12) | −0.0068 (14) | 0.0020 (13)
C11 | 0.0440 (16) | 0.0396 (16) | 0.0405 (16) | 0.0009 (12) | 0.0048 (13) | −0.0003 (12)
C12 | 0.0526 (18) | 0.0377 (15) | 0.0529 (18) | 0.0008 (14) | 0.0095 (14) | 0.0011 (13)
C13 | 0.0595 (19) | 0.0396 (16) | 0.0462 (19) | 0.0048 (13) | 0.0062 (14) | 0.0082 (13)
C14 | 0.0446 (16) | 0.0453 (16) | 0.0428 (17) | 0.0074 (12) | 0.0050 (14) | 0.0021 (13)
C15 | 0.0464 (16) | 0.0381 (16) | 0.0464 (17) | −0.0004 (13) | 0.0050 (13) | 0.0016 (12)
C16 | 0.0482 (17) | 0.0396 (15) | 0.0432 (17) | 0.0010 (13) | 0.0043 (13) | 0.0059 (13)
C17 | 0.0550 (19) | 0.061 (2) | 0.0503 (19) | −0.0044 (16) | −0.0028 (15) | 0.0035 (15)
C21 | 0.0439 (16) | 0.0383 (15) | 0.0482 (18) | 0.0037 (12) | −0.0056 (13) | −0.0018 (12)
C22 | 0.0511 (18) | 0.0375 (16) | 0.0530 (18) | −0.0005 (13) | −0.0054 (15) | −0.0027 (13)
C23 | 0.0587 (19) | 0.0419 (15) | 0.0491 (19) | 0.0014 (15) | −0.0078 (15) | −0.0095 (13)
C24 | 0.0453 (16) | 0.0438 (16) | 0.0444 (17) | 0.0066 (13) | −0.0016 (13) | −0.0049 (13)
C25 | 0.0459 (16) | 0.0398 (16) | 0.0478 (17) | −0.0018 (13) | −0.0018 (14) | −0.0040 (13)
C26 | 0.0486 (17) | 0.0400 (15) | 0.0478 (17) | 0.0019 (13) | −0.0026 (14) | −0.0082 (13)
C27 | 0.060 (2) | 0.062 (2) | 0.0529 (19) | −0.0114 (17) | 0.0086 (17) | −0.0079 (15)

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N1—C1 | 1.265 (4) | C12—H12 | 0.9500
N1—C2 | 1.467 (5) | C13—C14 | 1.388 (5)
N2—C5 | 1.271 (4) | C13—H13 | 0.9500
N2—C4 | 1.461 (4) | C14—C15 | 1.397 (5)
O1—C3 | 1.426 (4) | C15—C16 | 1.381 (5)
O1—H1 | 0.96 (5) | C15—H15 | 0.9500
O2—C14 | 1.370 (4) | C16—H16 | 0.9500
O2—C17 | 1.427 (4) | C17—H17A | 0.9800
O3—C24 | 1.367 (4) | C17—H17B | 0.9800
O3—C27 | 1.418 (4) | C17—H17C | 0.9800
C1—C11 | 1.474 (5) | C21—C26 | 1.397 (5)
C1—H1A | 0.9500 | C21—C22 | 1.398 (5)
C2—C3 | 1.525 (5) | C22—C23 | 1.376 (5)
C2—H2A | 0.9900 | C22—H22 | 0.9500
C2—H2B | 0.9900 | C23—C24 | 1.396 (5)
C3—C4 | 1.511 (5) | C23—H23 | 0.9500
C3—H3 | 1.0000 | C24—C25 | 1.395 (4)
C4—H4A | 0.9900 | C25—C26 | 1.391 (5)
C4—H4B | 0.9900 | C25—H25 | 0.9500
C5—C21 | 1.466 (5) | C26—H26 | 0.9500
C5—H5 | 0.9500 | C27—H27A | 0.9800
C11—C16 | 1.393 (4) | C27—H27B | 0.9800
C11—C12 | 1.402 (5) | C27—H27C | 0.9800
C12—C13 | 1.385 (5) |  |
C1—N1—C2 | 117.0 (3) | O2—C14—C15 | 124.8 (3)
C5—N2—C4 | 117.7 (3) | C13—C14—C15 | 119.8 (3)
C3—O1—H1 | 106 (3) | C16—C15—C14 | 119.6 (3)
C14—O2—C17 | 117.8 (3) | C16—C15—H15 | 120.2
C24—O3—C27 | 118.4 (3) | C14—C15—H15 | 120.2
N1—C1—C11 | 123.0 (3) | C15—C16—C11 | 121.4 (3)
N1—C1—H1A | 118.5 | C15—C16—H16 | 119.3
C11—C1—H1A | 118.5 | C11—C16—H16 | 119.3
N1—C2—C3 | 112.3 (3) | O2—C17—H17A | 109.5
N1—C2—H2A | 109.1 | O2—C17—H17B | 109.5
C3—C2—H2A | 109.1 | H17A—C17—H17B | 109.5
N1—C2—H2B | 109.1 | O2—C17—H17C | 109.5
C3—C2—H2B | 109.1 | H17A—C17—H17C | 109.5
H2A—C2—H2B | 107.9 | H17B—C17—H17C | 109.5
O1—C3—C4 | 108.6 (3) | C26—C21—C22 | 117.9 (3)
O1—C3—C2 | 109.0 (3) | C26—C21—C5 | 123.5 (3)
C4—C3—C2 | 110.8 (3) | C22—C21—C5 | 118.5 (3)
O1—C3—H3 | 109.5 | C23—C22—C21 | 121.6 (3)
C4—C3—H3 | 109.5 | C23—C22—H22 | 119.2
C2—C3—H3 | 109.5 | C21—C22—H22 | 119.2
N2—C4—C3 | 110.8 (3) | C22—C23—C24 | 120.0 (3)
N2—C4—H4A | 109.5 | C22—C23—H23 | 120.0
C3—C4—H4A | 109.5 | C24—C23—H23 | 120.0
N2—C4—H4B | 109.5 | O3—C24—C25 | 124.8 (3)
C3—C4—H4B | 109.5 | O3—C24—C23 | 115.7 (3)
H4A—C4—H4B | 108.1 | C25—C24—C23 | 119.5 (3)
N2—C5—C21 | 124.5 (3) | C26—C25—C24 | 119.8 (3)
N2—C5—H5 | 117.8 | C26—C25—H25 | 120.1
C21—C5—H5 | 117.8 | C24—C25—H25 | 120.1
C16—C11—C12 | 118.3 (3) | C25—C26—C21 | 121.2 (3)
C16—C11—C1 | 122.7 (3) | C25—C26—H26 | 119.4
C12—C11—C1 | 118.9 (3) | C21—C26—H26 | 119.4
C13—C12—C11 | 120.7 (3) | O3—C27—H27A | 109.5
C13—C12—H12 | 119.7 | O3—C27—H27B | 109.5
C11—C12—H12 | 119.7 | H27A—C27—H27B | 109.5
C12—C13—C14 | 120.2 (3) | O3—C27—H27C | 109.5
C12—C13—H13 | 119.9 | H27A—C27—H27C | 109.5
C14—C13—H13 | 119.9 | H27B—C27—H27C | 109.5
O2—C14—C13 | 115.4 (3) |  |
C2—N1—C1—C11 | 175.6 (3) | C13—C14—C15—C16 | −1.2 (4)
C1—N1—C2—C3 | 129.7 (3) | C14—C15—C16—C11 | 0.2 (5)
N1—C2—C3—O1 | 176.2 (3) | C12—C11—C16—C15 | 1.1 (5)
N1—C2—C3—C4 | −64.4 (4) | C1—C11—C16—C15 | −174.5 (3)
C5—N2—C4—C3 | 110.7 (3) | N2—C5—C21—C26 | −2.0 (5)
O1—C3—C4—N2 | −65.3 (3) | N2—C5—C21—C22 | 176.6 (3)
C2—C3—C4—N2 | 175.0 (3) | C26—C21—C22—C23 | 0.1 (5)
C4—N2—C5—C21 | −178.3 (3) | C5—C21—C22—C23 | −178.6 (3)
N1—C1—C11—C16 | 5.1 (5) | C21—C22—C23—C24 | 0.1 (5)
N1—C1—C11—C12 | −170.5 (3) | C27—O3—C24—C25 | 7.6 (5)
C16—C11—C12—C13 | −1.6 (5) | C27—O3—C24—C23 | −172.2 (3)
C1—C11—C12—C13 | 174.3 (3) | C22—C23—C24—O3 | 179.7 (3)
C11—C12—C13—C14 | 0.6 (5) | C22—C23—C24—C25 | −0.1 (5)
C17—O2—C14—C13 | 169.3 (3) | O3—C24—C25—C26 | −179.8 (3)
C17—O2—C14—C15 | −10.5 (5) | C23—C24—C25—C26 | 0.1 (5)
C12—C13—C14—O2 | −179.0 (3) | C24—C25—C26—C21 | 0.1 (5)
C12—C13—C14—C15 | 0.8 (5) | C22—C21—C26—C25 | −0.2 (5)
O2—C14—C15—C16 | 178.6 (3) | C5—C21—C26—C25 | 178.4 (3)

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D—H···A | D—H | H···A | D···A | D—H···A
O1—H1···N2i | 0.96 (5) | 1.80 (5) | 2.761 (4) | 175 (4)
C17—H17B···O3ii | 0.98 | 2.63 | 3.447 (5) | 142
C27—H27B···O2iii | 0.98 | 2.65 | 3.415 (4) | 135
C12—H12···Cg1iv | 0.95 | 2.99 | 3.658 (4) | 129
C22—H22···Cg2iv | 0.95 | 2.92 | 3.628 (3) | 132

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Figure 1.

The molecular structure of the title compound, Displacement ellipsoids are drawn at the 50% probability level.

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Figure 2.

Partial packing diagram of the title compound, showing an extended hydrogen-bonded network. H atoms not involved in hydrogen bonds have been omitted for clarity.

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Table 1. Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C11–C16 and C21–C26 rings, respectively.

D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A
O1—H1⋯N2i | 0.96 (5) | 1.80 (5) | 2.761 (4) | 175 (4)
C17—H17B⋯O3ii | 0.98 | 2.63 | 3.447 (5) | 142
C27—H27B⋯O2iii | 0.98 | 2.65 | 3.415 (4) | 135
C12—H12⋯Cg1iv | 0.95 | 2.99 | 3.658 (4) | 129
C22—H22⋯Cg2iv | 0.95 | 2.92 | 3.628 (3) | 132

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

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Table 2. Experimental details

Crystal data
Chemical formula | C₁₉H₂₂N₂O₃
M r | 326.38
Crystal system, space group | Orthorhombic, P n a2₁
Temperature (K) | 173
a, b, c (Å) | 7.9081 (3), 5.8434 (3), 37.4435 (16)
V (Å³) | 1730.27 (13)
Z | 4
Radiation type | Mo Kα
μ (mm⁻¹) | 0.09
Crystal size (mm) | 0.28 × 0.19 × 0.08
Data collection
Diffractometer | Stoe IPDS II two-circle
Absorption correction | Multi-scan (X-AREA; Stoe & Cie, 2001 ▸)
T min, T max | 0.625, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections | 12316, 3084, 2786
R int | 0.038
(sin θ/λ)max (Å⁻¹) | 0.608
Refinement
R[F ² > 2σ(F ²)], wR(F ²), S | 0.046, 0.123, 1.01
No. of reflections | 3084
No. of parameters | 224
No. of restraints | 1
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å⁻³) | 0.15, −0.16

Computer programs: X-AREA (Stoe & Cie, 2001 ▸), SHELXS97 (Sheldrick, 2008 ▸), SHELXL2014 (Sheldrick, 2015 ▸) and XP in SHELXTL-Plus (Sheldrick, 2008 ▸).

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