Acta Crystallographica Section E: Crystallographic Communications

Acta Crystallogr E Crystallogr Commun. 73(Pt 6): 813-816

1,3-Bis{(E)-[4-(dimethylamino)benzylidene]amino}propan-2-ol: chain structure formation via an O—H⋯N hydrogen bond

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-Str. 7, 60438 Frankfurt/Main, Germany

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

© Rivera et al. 2017

DOI: 10.1107/S2056989017006429

Published online: 05 May 2017

Abstract

The molecular and crystal structure of the title Schiff base derivative is reported. O—H⋯N hydrogen bonds link molecules into a supramolecular chain along a.

Abstract

The asymmetric unit of the title compound, C₂₁H₂₈N₄O, consists of two unique molecules linked by an O—H⋯N hydrogen bond. The conformation of both C=N bonds is E and the azomethine functional groups lie close to the plane of their associated benzene rings in each of the independent molecules. The dihedral angles between the two benzene rings are 83.14 (4) and 75.45 (4)°. The plane of the one of the N(CH₃)₂ units is twisted away from the benzene ring by 18.8 (2)°, indicating loss of conjugation between the lone electron pair and the benzene ring. In the crystal structure, O—H⋯N hydrogen bonds together with C—H⋯O hydrogen bonds link neighbouring supramolecular dimers into a three-dimensional network.

Chemical context  

Schiff bases play important roles in the development of coordination chemistry related to catalysis, enzymatic reactions, and supramolecular architectures. Crystal structures of Schiff bases derived from substituted benzaldehydes and 1,3-diaminopropan-2-ol have been reported earlier (Azam, Warad, Al-Resayes et al., 2012 ▸; Azam, Hussain et al., 2012 ▸; Rivera et al., 2016b ▸, 2017 ▸; Elmali, 2000 ▸). The title compound, (I), acts as an important raw material for the synthesis of Schiff base complexes. As an extension of our work on the synthesis and structural characterization of such Schiff base compounds, the crystal structure of the title compound is reported here.

Structural commentary  

The title compound crystallizes with two unique molecules in the asymmetric unit. The conformers, labeled A and B, are shown in Fig. 1 ▸. Each molecule comprises a 1,3-diamino-2-hydroxypropane bridge symmetrically substituted at the 1 and 3 positions by 4-(dimethylamino)phenyl]methylidene units. The conformational differences between the two molecules are extremely small, resulting in a superstructural motif. The two molecules are related by translation along the a-axis direction. A structural overlay of the two independent molecules (r.m.s. deviation for fitting all non-H atoms = 0.097 Å) is shown in Fig. 2 ▸. The disposition of the residues attached to the N2A and N2 positions can be described by the torsion angles N2A—C5A—C51A—C56A [−9.9 (11) in molecule A] and N2—C5—C51—C56 [−14.9 (11)° in molecule B]. The two outer aromatic rings (C11–C16 and C51–C56) are inclined to one another by 83.14 (4)° in molecule A and 75.45 (4)° in molecule B.

Bond distances and angles in the benzene rings are not unusual and compare well, both between the two independent molecules and with those observed in related systems (see for example: Rivera et al., 2016b ▸). The values for the azomethine C=N bond distances in the two molecules [1.275 (8) and 1.272 (8) in molecule A and 1.271 (8) and 1.269 (8) Å in molecule B] and the corresponding internal angles at the nitrogen atom [C1A—N1A—C2A = 117.7 (6) and C5A—N2A—C4A = 117.7 (6) in molecule A and C1—N1—C2 = 117.5 (6) and C5—N2—C4 = 117.6 (6) in molecule B] also agree with those reported in the literature for similar compounds (Rivera et al., 2016b ▸) and are consistent with C=N double bonding. In both molecules, the azomethine groups adopt an E,E conformation, as can be seen from the torsion angles C2A—N1A—C1A—C11A = 177.8 (6)° and C4A—N2A—C5A—C51A = 179.9 (6)° in molecule A and C2—N1—C1—C11 = 178.6 (6)° and C4—N2—C5—C51 = 177.0 (6) in molecule B.

The two dimethylamino substituents in molecule B are essentially coplanar with the benzene rings to which they are bound with torsion angles C17—N3—C14—C13 = −3.1 (11)° and C57—N4—C54—C53 = −2.9 (11)° and with dihedral angles between the NMe₂ plane and the benzene ring of 0.57 (2) and 4.60 (2)°, respectively, whilst in molecule A the corresponding torsional angles C17A—N3A—C14A—C13A and C57A—N4A—C54A—C53A are 2.2 (11) and 8.3 (10)°, respectively. The dihedral angles between the two dimethylamino groups (N3A and N4A) and the benzene rings are 5.09 (22) and 18.8 (2)° respectively, indicating that the lone electron pair of the N4A atom may not be completely conjugated with the benzene ring (C51A–C56A).

Supramolecular features  

Through O—H⋯N hydrogen-bonding interactions [2.863 (7) Å] between O1A—H1A and the nitrogen N2 (Table 1 ▸), the two independent molecules interact to form C(5) chains running along the a axis (Fig. 3 ▸). The chains are linked into a three-dimensional framework by a pair of weaker intermolecular C57—H57B⋯O1ii and C57A—H57E⋯O1A iii hydrogen bonds (Table 1 ▸).

Database survey  

A search in the Cambridge Crystallographic Database (Groom et al., 2016 ▸) for the fragment 1,3-bis[(benzylidene)amino]propan-2-ol yielded the following structures: N,N′-[(2-hydroxy-1,3-propanediyl)bis(nitrilomethylylidene-2,1-phenylene)]bis(4-methylbenzenesulfonamide) (Popov et al., 2009 ▸), 2,2′-[(2-hydroxypropane-1,3-diyl)bis(nitrilomethylylidene)]diphenol (Azam, Hussain et al., 2012 ▸), 1,3-bis(2-hydroxy-5-bromosalicylideneamine)propan-2-ol (Elmali, 2000 ▸), 1,3-bis[(E)-(2-chlorobenzylidene)amino]propan-2-ol (Azam, Warad, Al-Resayes et al., 2012 ▸) and 1,3-bis[(4-methoxybenzylidene)amino]propan-2-ol (Rivera et al. 2016b ▸). In each of these structures, the N=C double bonds adopt E conformations.

Synthesis and crystallization  

The title compound was prepared as described by (Rivera et al. 2016a ▸). The crude product was recrystallized from diethyl ether solution by slow evaporation of the solvent, giving colorless crystals suitable for X–ray diffraction (m.p. 396.8–398 K; yield 40%).

Refinement  

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The coordinates of the hydroxyl H atom were refined with U iso(H) = 1.5U eq(O). 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) = 0.98 Å for methyl, d(C—H) = 0.99 Å for methylene, d(C—H) = 1.00 Å for tertiary CH. The U iso(H) values were constrained to 1.5U eq(Cmethyl) or 1.2U eq(C) for the remaining H atoms. The structure shows signs of a superstructure. The two molecules are related by a translation of 1/2 along the a axis. However, if the structure is refined in a cell with the a axis halved, the displacement parameters of one NMe₂ group and some of the C atoms of the phenyl ring to which this group is attached are significantly enlarged (Fig. 4 ▸). Shifting one molecule by ½ in the a-axis direction, it becomes obvious how similar the two molecules are. Nevertheless, there are small differences in their overall conformation (Fig. 5 ▸). As a result of that, we opted to refine the structure using the larger unit cell with two molecules in the asymmetric unit.

Figure 1View larger versionFigure 1. The structure of the independent molecules A and B, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level for non-H atoms.

Figure 2View larger versionFigure 2. The structural overlay of the independent molecules A (green dashed) and B (purple) of the title compound.

Figure 3View larger versionFigure 3. Crystal packing of the title compound, indicating the O—H⋯N hydrogen bonds (dashed lines), which result in chains along the a-axis direction.

Figure 4View larger versionFigure 4. Perspective view of the molecule if the structure is refined in a cell with the a axis halved.

Figure 5View larger versionFigure 5. Partial packing diagram of the title compound with one molecule shifted by x = ½, y = 0, z = 0, showing similarities and differences between the two molecules.

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

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. 35816). IMC is also grateful to COLCIENCIAS for his 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)

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Hydrogen-bond geometry (Å, º)

See full table

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

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References

Azam, M., Hussain, U., Warad, I., Al-Resayes, S. I., Khan, Md. S., Shakir, Md., Trzesowska-Kruszynska, A. & Kruszynski, R. (2012). Dalton Trans. 41, 10854–10864.

Azam, M., Warad, I., Al-Resayes, S. I., Shakir, M., Ullah, M. F., Ahmad, A. & Sarkar, F. H. (2012). Inorg. Chem. Commun. 20, 252–258.

Elmali, A. (2000). J. Chem. Crystallogr. 30, 473–477.

Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179.

Popov, L. D., Tupolova, Yu. P., Lukov, V. V., Shcherbakov, I. N., Burlov, A. S., Levchenkov, S. I., Kogan, V. A., Lyssenko, K. A. & Ivannikova, E. V. (2009). Inorg. Chim. Acta, 362, 1673–1680.

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

Rivera, A., Miranda-Carvajal, I., Ríos-Motta, J. & Bolte, M. (2016b). Acta Cryst. E72, 1731–1733.

Rivera, A., Miranda-Carvajal, I., Ríos-Motta, J. & Bolte, M. (2017). Acta Cryst. E73, 627–629.

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

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

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

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C₂₁H₂₈N₄O | F(000) = 760
Mr = 352.47 | Dx = 1.220 Mg m⁻³
Monoclinic, P2₁ | Mo Kα radiation, λ = 0.71073 Å
a = 9.1456 (10) Å | Cell parameters from 8852 reflections
b = 10.5860 (8) Å | θ = 3.2–25.9°
c = 19.974 (2) Å | µ = 0.08 mm⁻¹
β = 97.110 (9)° | T = 173 K
V = 1918.9 (3) Å³ | Needle, colourless
Z = 4 | 0.22 × 0.03 × 0.03 mm

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STOE IPDS II two-circle-diffractometer | 3688 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.069
ω scans | θmax = 25.7°, θmin = 3.2°
Absorption correction: multi-scan (X-Area; Stoe & Cie, 2001) | h = −11→11
Tmin = 0.426, Tmax = 1.000 | k = −11→12
16633 measured reflections | l = −24→24
6852 independent reflections |

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Refinement on F² | 1 restraint
Least-squares matrix: full | Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.063 | H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.156 | w = 1/[σ²(Fo²) + (0.0713P)²] where P = (Fo² + 2Fc²)/3
S = 0.93 | (Δ/σ)max < 0.001
6852 reflections | Δρmax = 0.17 e Å⁻³
483 parameters | Δρmin = −0.22 e Å⁻³

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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 |
O1 | −0.2650 (5) | 0.6469 (4) | 0.2463 (2) | 0.0338 (11) |
H1 | −0.333 (9) | 0.594 (7) | 0.243 (4) | 0.051* |
N1 | −0.0704 (6) | 0.5677 (5) | 0.4156 (3) | 0.0337 (13) |
N2 | −0.0059 (6) | 0.4851 (5) | 0.2177 (3) | 0.0325 (13) |
N3 | 0.4143 (8) | 0.5502 (6) | 0.6804 (3) | 0.056 (2) |
N4 | 0.1885 (8) | 0.4185 (7) | −0.0846 (3) | 0.0525 (18) |
C1 | −0.0252 (7) | 0.6501 (6) | 0.4596 (3) | 0.0318 (15) |
H1B | −0.0717 | 0.7305 | 0.4578 | 0.038* |
C2 | −0.1945 (7) | 0.6018 (7) | 0.3656 (3) | 0.0329 (15) |
H2A | −0.2318 | 0.6862 | 0.3764 | 0.040* |
H2B | −0.2752 | 0.5401 | 0.3672 | 0.040* |
C3 | −0.1482 (7) | 0.6038 (6) | 0.2949 (3) | 0.0280 (14) |
H3 | −0.0654 | 0.6657 | 0.2953 | 0.034* |
C4 | −0.0905 (7) | 0.4759 (6) | 0.2754 (3) | 0.0295 (14) |
H4A | −0.0268 | 0.4401 | 0.3145 | 0.035* |
H4B | −0.1745 | 0.4177 | 0.2640 | 0.035* |
C5 | −0.0408 (7) | 0.4112 (6) | 0.1683 (3) | 0.0291 (14) |
H5 | −0.1163 | 0.3509 | 0.1720 | 0.035* |
C11 | 0.0959 (7) | 0.6257 (6) | 0.5131 (3) | 0.0286 (14) |
C12 | 0.1407 (8) | 0.7210 (6) | 0.5603 (3) | 0.0349 (16) |
H12 | 0.0966 | 0.8023 | 0.5552 | 0.042* |
C13 | 0.2491 (8) | 0.6979 (6) | 0.6143 (3) | 0.0346 (16) |
H13 | 0.2791 | 0.7642 | 0.6451 | 0.041* |
C14 | 0.3151 (8) | 0.5775 (6) | 0.6241 (3) | 0.0340 (16) |
C15 | 0.2724 (7) | 0.4838 (6) | 0.5751 (3) | 0.0313 (15) |
H15 | 0.3170 | 0.4027 | 0.5792 | 0.038* |
C16 | 0.1666 (7) | 0.5092 (6) | 0.5215 (3) | 0.0282 (14) |
H16 | 0.1408 | 0.4448 | 0.4891 | 0.034* |
C17 | 0.4596 (10) | 0.6471 (7) | 0.7298 (4) | 0.050 (2) |
H17A | 0.5096 | 0.7152 | 0.7084 | 0.075* |
H17B | 0.5272 | 0.6106 | 0.7667 | 0.075* |
H17C | 0.3728 | 0.6810 | 0.7478 | 0.075* |
C18 | 0.4822 (8) | 0.4275 (7) | 0.6890 (4) | 0.0458 (18) |
H18A | 0.4071 | 0.3642 | 0.6956 | 0.069* |
H18B | 0.5574 | 0.4287 | 0.7285 | 0.069* |
H18C | 0.5283 | 0.4061 | 0.6487 | 0.069* |
C51 | 0.0284 (8) | 0.4128 (7) | 0.1056 (3) | 0.0330 (16) |
C52 | 0.0002 (8) | 0.3146 (7) | 0.0598 (3) | 0.0431 (17) |
H52 | −0.0583 | 0.2455 | 0.0713 | 0.052* |
C53 | 0.0546 (9) | 0.3135 (8) | −0.0025 (3) | 0.0458 (19) |
H53 | 0.0343 | 0.2439 | −0.0322 | 0.055* |
C54 | 0.1384 (8) | 0.4140 (8) | −0.0211 (4) | 0.0390 (17) |
C55 | 0.1671 (8) | 0.5154 (7) | 0.0254 (3) | 0.0376 (17) |
H55 | 0.2227 | 0.5861 | 0.0138 | 0.045* |
C56 | 0.1155 (8) | 0.5119 (7) | 0.0867 (3) | 0.0351 (16) |
H56 | 0.1396 | 0.5792 | 0.1175 | 0.042* |
C57 | 0.1555 (11) | 0.3106 (9) | −0.1292 (4) | 0.066 (3) |
H57A | 0.1979 | 0.2340 | −0.1072 | 0.099* |
H57B | 0.1980 | 0.3246 | −0.1713 | 0.099* |
H57C | 0.0485 | 0.3008 | −0.1392 | 0.099* |
C58 | 0.2838 (10) | 0.5179 (9) | −0.1020 (4) | 0.059 (2) |
H58A | 0.2329 | 0.5992 | −0.1009 | 0.089* |
H58B | 0.3103 | 0.5030 | −0.1474 | 0.089* |
H58C | 0.3734 | 0.5193 | −0.0695 | 0.089* |
O1A | 0.2364 (5) | 0.6551 (4) | 0.2491 (2) | 0.0307 (10) |
H1A | 0.175 (9) | 0.598 (7) | 0.236 (4) | 0.046* |
N1A | 0.4307 (6) | 0.5729 (5) | 0.4178 (2) | 0.0321 (13) |
N2A | 0.4841 (6) | 0.4805 (5) | 0.2205 (3) | 0.0272 (12) |
N3A | 0.9201 (8) | 0.5491 (6) | 0.6802 (3) | 0.0528 (18) |
N4A | 0.6733 (7) | 0.3641 (7) | −0.0786 (3) | 0.0493 (16) |
C1A | 0.4784 (8) | 0.6543 (6) | 0.4623 (3) | 0.0320 (15) |
H1A1 | 0.4335 | 0.7353 | 0.4603 | 0.038* |
C2A | 0.3069 (7) | 0.6088 (6) | 0.3686 (3) | 0.0301 (14) |
H2A1 | 0.2727 | 0.6943 | 0.3792 | 0.036* |
H2A2 | 0.2244 | 0.5490 | 0.3710 | 0.036* |
C3A | 0.3525 (7) | 0.6076 (6) | 0.2969 (3) | 0.0267 (14) |
H3A | 0.4386 | 0.6658 | 0.2967 | 0.032* |
C4A | 0.4027 (8) | 0.4766 (6) | 0.2788 (3) | 0.0314 (15) |
H4A1 | 0.4663 | 0.4404 | 0.3178 | 0.038* |
H4A2 | 0.3156 | 0.4210 | 0.2688 | 0.038* |
C5A | 0.4427 (8) | 0.4067 (6) | 0.1714 (3) | 0.0295 (15) |
H5A | 0.3609 | 0.3534 | 0.1759 | 0.035* |
C11A | 0.5983 (7) | 0.6298 (6) | 0.5160 (3) | 0.0261 (14) |
C12A | 0.6474 (7) | 0.7222 (6) | 0.5632 (3) | 0.0317 (15) |
H12A | 0.6067 | 0.8047 | 0.5582 | 0.038* |
C13A | 0.7528 (8) | 0.6973 (6) | 0.6165 (3) | 0.0345 (16) |
H13A | 0.7825 | 0.7622 | 0.6481 | 0.041* |
C14A | 0.8175 (8) | 0.5775 (6) | 0.6252 (3) | 0.0336 (15) |
C15A | 0.7757 (8) | 0.4861 (6) | 0.5758 (3) | 0.0355 (16) |
H15A | 0.8212 | 0.4053 | 0.5791 | 0.043* |
C16A | 0.6686 (7) | 0.5124 (6) | 0.5223 (3) | 0.0295 (14) |
H16A | 0.6423 | 0.4492 | 0.4892 | 0.035* |
C17A | 0.9607 (10) | 0.6408 (7) | 0.7321 (4) | 0.052 (2) |
H17D | 1.0069 | 0.7135 | 0.7128 | 0.077* |
H17E | 1.0305 | 0.6029 | 0.7676 | 0.077* |
H17F | 0.8725 | 0.6686 | 0.7512 | 0.077* |
C18A | 0.9840 (8) | 0.4245 (7) | 0.6888 (4) | 0.0457 (18) |
H18D | 0.9081 | 0.3642 | 0.6985 | 0.069* |
H18E | 1.0637 | 0.4255 | 0.7264 | 0.069* |
H18F | 1.0235 | 0.3994 | 0.6474 | 0.069* |
C51A | 0.5096 (8) | 0.3966 (6) | 0.1087 (3) | 0.0304 (16) |
C52A | 0.4621 (8) | 0.3029 (6) | 0.0628 (3) | 0.0386 (16) |
H52A | 0.3901 | 0.2446 | 0.0740 | 0.046* |
C53A | 0.5148 (9) | 0.2908 (7) | 0.0017 (4) | 0.0457 (18) |
H53A | 0.4794 | 0.2247 | −0.0282 | 0.055* |
C54A | 0.6205 (9) | 0.3753 (8) | −0.0169 (3) | 0.0409 (19) |
C55A | 0.6708 (8) | 0.4707 (8) | 0.0289 (3) | 0.0403 (17) |
H55A | 0.7434 | 0.5288 | 0.0180 | 0.048* |
C56A | 0.6136 (8) | 0.4806 (7) | 0.0914 (3) | 0.0371 (17) |
H56A | 0.6475 | 0.5462 | 0.1219 | 0.045* |
C57A | 0.6067 (10) | 0.2760 (8) | −0.1289 (3) | 0.063 (3) |
H57D | 0.6115 | 0.1904 | −0.1100 | 0.095* |
H57E | 0.6600 | 0.2786 | −0.1685 | 0.095* |
H57F | 0.5034 | 0.2993 | −0.1421 | 0.095* |
C58A | 0.7565 (10) | 0.4673 (10) | −0.1032 (4) | 0.065 (3) |
H58D | 0.6943 | 0.5429 | −0.1090 | 0.097* |
H58E | 0.7881 | 0.4437 | −0.1466 | 0.097* |
H58F | 0.8433 | 0.4850 | −0.0706 | 0.097* |

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| U ¹¹ | U ²² | U ³³ | U ¹² | U ¹³ | U ²³
O1 | 0.038 (3) | 0.032 (3) | 0.031 (2) | −0.002 (2) | −0.002 (2) | 0.0081 (19)
N1 | 0.038 (3) | 0.036 (3) | 0.028 (3) | 0.002 (2) | 0.009 (3) | −0.001 (2)
N2 | 0.034 (3) | 0.034 (3) | 0.030 (3) | 0.006 (2) | 0.006 (2) | 0.001 (2)
N3 | 0.081 (5) | 0.032 (4) | 0.047 (4) | −0.005 (3) | −0.027 (4) | 0.001 (3)
N4 | 0.051 (4) | 0.078 (5) | 0.030 (3) | 0.005 (4) | 0.009 (3) | −0.013 (3)
C1 | 0.029 (4) | 0.032 (4) | 0.035 (4) | 0.009 (3) | 0.007 (3) | 0.000 (3)
C2 | 0.028 (4) | 0.041 (4) | 0.031 (3) | 0.003 (3) | 0.007 (3) | 0.001 (3)
C3 | 0.028 (3) | 0.026 (3) | 0.030 (3) | 0.001 (3) | 0.005 (3) | 0.000 (2)
C4 | 0.030 (3) | 0.032 (3) | 0.027 (3) | −0.005 (3) | 0.004 (3) | 0.006 (3)
C5 | 0.027 (3) | 0.028 (3) | 0.031 (3) | −0.002 (3) | −0.002 (3) | −0.002 (3)
C11 | 0.026 (3) | 0.032 (3) | 0.030 (3) | −0.002 (3) | 0.012 (3) | −0.001 (3)
C12 | 0.043 (4) | 0.025 (3) | 0.036 (4) | 0.001 (3) | 0.002 (3) | 0.002 (3)
C13 | 0.044 (4) | 0.026 (3) | 0.034 (4) | −0.008 (3) | 0.006 (3) | −0.008 (3)
C14 | 0.040 (4) | 0.033 (4) | 0.028 (3) | −0.009 (3) | 0.001 (3) | 0.008 (3)
C15 | 0.036 (4) | 0.024 (3) | 0.033 (3) | −0.003 (3) | 0.003 (3) | 0.001 (2)
C16 | 0.027 (3) | 0.027 (3) | 0.031 (3) | −0.005 (3) | 0.006 (3) | −0.004 (2)
C17 | 0.064 (5) | 0.046 (4) | 0.037 (4) | −0.012 (4) | −0.010 (4) | −0.002 (3)
C18 | 0.054 (5) | 0.043 (4) | 0.037 (4) | −0.004 (4) | −0.005 (3) | 0.009 (3)
C51 | 0.038 (4) | 0.035 (4) | 0.025 (3) | 0.013 (3) | 0.002 (3) | −0.005 (3)
C52 | 0.050 (4) | 0.044 (4) | 0.035 (4) | 0.004 (3) | 0.003 (3) | 0.001 (3)
C53 | 0.054 (4) | 0.052 (4) | 0.030 (3) | 0.009 (4) | 0.000 (3) | −0.018 (3)
C54 | 0.033 (4) | 0.052 (4) | 0.032 (3) | 0.007 (3) | 0.001 (3) | −0.004 (3)
C55 | 0.038 (4) | 0.047 (4) | 0.027 (3) | 0.001 (3) | −0.001 (3) | −0.004 (3)
C56 | 0.031 (4) | 0.044 (4) | 0.031 (3) | −0.004 (3) | 0.003 (3) | −0.008 (3)
C57 | 0.086 (6) | 0.073 (6) | 0.038 (4) | 0.029 (5) | 0.008 (4) | −0.017 (4)
C58 | 0.054 (5) | 0.088 (6) | 0.041 (4) | 0.015 (4) | 0.030 (4) | 0.012 (4)
O1A | 0.031 (3) | 0.035 (3) | 0.026 (2) | 0.000 (2) | 0.0010 (19) | 0.0069 (18)
N1A | 0.032 (3) | 0.038 (3) | 0.026 (3) | 0.002 (2) | 0.003 (2) | −0.003 (2)
N2A | 0.028 (3) | 0.025 (3) | 0.027 (3) | 0.003 (2) | 0.001 (2) | −0.002 (2)
N3A | 0.068 (5) | 0.037 (4) | 0.044 (3) | −0.004 (3) | −0.030 (3) | 0.003 (3)
N4A | 0.046 (4) | 0.074 (4) | 0.029 (3) | 0.004 (3) | 0.011 (3) | −0.012 (3)
C1A | 0.037 (4) | 0.033 (4) | 0.027 (4) | 0.002 (3) | 0.007 (3) | −0.005 (3)
C2A | 0.032 (4) | 0.033 (4) | 0.025 (3) | −0.002 (3) | 0.007 (3) | −0.001 (3)
C3A | 0.029 (3) | 0.027 (3) | 0.025 (3) | −0.003 (3) | 0.005 (3) | 0.000 (2)
C4A | 0.039 (4) | 0.029 (3) | 0.026 (3) | 0.005 (3) | 0.005 (3) | 0.003 (3)
C5A | 0.032 (4) | 0.023 (3) | 0.032 (3) | 0.006 (3) | 0.001 (3) | 0.006 (2)
C11A | 0.028 (3) | 0.027 (3) | 0.023 (3) | −0.001 (3) | 0.004 (3) | 0.000 (2)
C12A | 0.037 (4) | 0.025 (3) | 0.034 (3) | 0.003 (3) | 0.004 (3) | −0.005 (3)
C13A | 0.040 (4) | 0.035 (4) | 0.027 (3) | −0.005 (3) | −0.002 (3) | −0.002 (3)
C14A | 0.031 (4) | 0.032 (4) | 0.036 (4) | −0.002 (3) | −0.003 (3) | 0.000 (3)
C15A | 0.045 (4) | 0.024 (3) | 0.037 (4) | −0.004 (3) | 0.004 (3) | 0.003 (3)
C16A | 0.035 (4) | 0.027 (3) | 0.026 (3) | −0.008 (3) | 0.004 (3) | −0.001 (2)
C17A | 0.064 (5) | 0.044 (4) | 0.040 (4) | −0.007 (4) | −0.021 (4) | −0.003 (3)
C18A | 0.046 (4) | 0.040 (4) | 0.047 (4) | −0.002 (4) | −0.014 (3) | 0.015 (3)
C51A | 0.027 (3) | 0.033 (4) | 0.029 (3) | 0.006 (3) | −0.004 (3) | −0.003 (2)
C52A | 0.052 (4) | 0.031 (3) | 0.031 (3) | 0.005 (3) | 0.003 (3) | −0.006 (3)
C53A | 0.060 (5) | 0.042 (4) | 0.034 (3) | 0.008 (4) | 0.001 (3) | −0.008 (3)
C54A | 0.036 (4) | 0.057 (5) | 0.028 (3) | 0.024 (4) | −0.005 (3) | −0.014 (3)
C55A | 0.027 (3) | 0.065 (5) | 0.029 (3) | 0.001 (3) | 0.006 (3) | −0.007 (3)
C56A | 0.032 (4) | 0.053 (4) | 0.026 (3) | 0.002 (3) | 0.001 (3) | −0.008 (3)
C57A | 0.090 (6) | 0.074 (6) | 0.024 (3) | 0.038 (5) | 0.001 (4) | −0.017 (3)
C58A | 0.059 (5) | 0.097 (7) | 0.037 (4) | 0.021 (5) | 0.005 (4) | 0.001 (4)

[Back]

[Back]

O1—C3 | 1.426 (7) | O1A—C3A | 1.429 (7)
O1—H1 | 0.84 (8) | O1A—H1A | 0.84 (8)
N1—C1 | 1.271 (8) | N1A—C1A | 1.275 (8)
N1—C2 | 1.461 (8) | N1A—C2A | 1.454 (8)
N2—C5 | 1.269 (8) | N2A—C5A | 1.272 (8)
N2—C4 | 1.470 (8) | N2A—C4A | 1.460 (8)
N3—C14 | 1.386 (9) | N3A—C14A | 1.388 (8)
N3—C18 | 1.440 (10) | N3A—C17A | 1.434 (9)
N3—C17 | 1.448 (9) | N3A—C18A | 1.444 (10)
N4—C54 | 1.400 (9) | N4A—C54A | 1.383 (9)
N4—C58 | 1.436 (11) | N4A—C57A | 1.449 (10)
N4—C57 | 1.458 (11) | N4A—C58A | 1.452 (12)
C1—C11 | 1.463 (9) | C1A—C11A | 1.459 (8)
C1—H1B | 0.9500 | C1A—H1A1 | 0.9500
C2—C3 | 1.523 (9) | C2A—C3A | 1.542 (8)
C2—H2A | 0.9900 | C2A—H2A1 | 0.9900
C2—H2B | 0.9900 | C2A—H2A2 | 0.9900
C3—C4 | 1.521 (9) | C3A—C4A | 1.518 (8)
C3—H3 | 1.0000 | C3A—H3A | 1.0000
C4—H4A | 0.9900 | C4A—H4A1 | 0.9900
C4—H4B | 0.9900 | C4A—H4A2 | 0.9900
C5—C51 | 1.472 (10) | C5A—C51A | 1.465 (10)
C5—H5 | 0.9500 | C5A—H5A | 0.9500
C11—C16 | 1.393 (9) | C11A—C12A | 1.394 (9)
C11—C12 | 1.407 (9) | C11A—C16A | 1.397 (9)
C12—C13 | 1.395 (10) | C12A—C13A | 1.371 (9)
C12—H12 | 0.9500 | C12A—H12A | 0.9500
C13—C14 | 1.413 (10) | C13A—C14A | 1.400 (9)
C13—H13 | 0.9500 | C13A—H13A | 0.9500
C14—C15 | 1.415 (9) | C14A—C15A | 1.400 (9)
C15—C16 | 1.377 (9) | C15A—C16A | 1.386 (9)
C15—H15 | 0.9500 | C15A—H15A | 0.9500
C16—H16 | 0.9500 | C16A—H16A | 0.9500
C17—H17A | 0.9800 | C17A—H17D | 0.9800
C17—H17B | 0.9800 | C17A—H17E | 0.9800
C17—H17C | 0.9800 | C17A—H17F | 0.9800
C18—H18A | 0.9800 | C18A—H18D | 0.9800
C18—H18B | 0.9800 | C18A—H18E | 0.9800
C18—H18C | 0.9800 | C18A—H18F | 0.9800
C51—C52 | 1.387 (10) | C51A—C56A | 1.377 (10)
C51—C56 | 1.397 (10) | C51A—C52A | 1.384 (9)
C52—C53 | 1.397 (10) | C52A—C53A | 1.373 (10)
C52—H52 | 0.9500 | C52A—H52A | 0.9500
C53—C54 | 1.388 (11) | C53A—C54A | 1.399 (12)
C53—H53 | 0.9500 | C53A—H53A | 0.9500
C54—C55 | 1.423 (10) | C54A—C55A | 1.401 (10)
C55—C56 | 1.365 (10) | C55A—C56A | 1.416 (10)
C55—H55 | 0.9500 | C55A—H55A | 0.9500
C56—H56 | 0.9500 | C56A—H56A | 0.9500
C57—H57A | 0.9800 | C57A—H57D | 0.9800
C57—H57B | 0.9800 | C57A—H57E | 0.9800
C57—H57C | 0.9800 | C57A—H57F | 0.9800
C58—H58A | 0.9800 | C58A—H58D | 0.9800
C58—H58B | 0.9800 | C58A—H58E | 0.9800
C58—H58C | 0.9800 | C58A—H58F | 0.9800
C3—O1—H1 | 109 (5) | C3A—O1A—H1A | 112 (5)
C1—N1—C2 | 117.5 (6) | C1A—N1A—C2A | 117.7 (6)
C5—N2—C4 | 117.6 (6) | C5A—N2A—C4A | 117.7 (6)
C14—N3—C18 | 121.0 (6) | C14A—N3A—C17A | 121.0 (6)
C14—N3—C17 | 120.6 (6) | C14A—N3A—C18A | 121.1 (6)
C18—N3—C17 | 118.3 (6) | C17A—N3A—C18A | 117.9 (6)
C54—N4—C58 | 121.4 (7) | C54A—N4A—C57A | 120.6 (7)
C54—N4—C57 | 117.5 (7) | C54A—N4A—C58A | 119.6 (7)
C58—N4—C57 | 120.7 (7) | C57A—N4A—C58A | 116.2 (6)
N1—C1—C11 | 122.4 (6) | N1A—C1A—C11A | 123.6 (6)
N1—C1—H1B | 118.8 | N1A—C1A—H1A1 | 118.2
C11—C1—H1B | 118.8 | C11A—C1A—H1A1 | 118.2
N1—C2—C3 | 110.8 (5) | N1A—C2A—C3A | 110.4 (5)
N1—C2—H2A | 109.5 | N1A—C2A—H2A1 | 109.6
C3—C2—H2A | 109.5 | C3A—C2A—H2A1 | 109.6
N1—C2—H2B | 109.5 | N1A—C2A—H2A2 | 109.6
C3—C2—H2B | 109.5 | C3A—C2A—H2A2 | 109.6
H2A—C2—H2B | 108.1 | H2A1—C2A—H2A2 | 108.1
O1—C3—C4 | 111.4 (5) | O1A—C3A—C4A | 112.6 (5)
O1—C3—C2 | 111.3 (5) | O1A—C3A—C2A | 110.8 (5)
C4—C3—C2 | 111.7 (5) | C4A—C3A—C2A | 110.6 (5)
O1—C3—H3 | 107.4 | O1A—C3A—H3A | 107.5
C4—C3—H3 | 107.4 | C4A—C3A—H3A | 107.5
C2—C3—H3 | 107.4 | C2A—C3A—H3A | 107.5
N2—C4—C3 | 112.0 (5) | N2A—C4A—C3A | 111.3 (5)
N2—C4—H4A | 109.2 | N2A—C4A—H4A1 | 109.4
C3—C4—H4A | 109.2 | C3A—C4A—H4A1 | 109.4
N2—C4—H4B | 109.2 | N2A—C4A—H4A2 | 109.4
C3—C4—H4B | 109.2 | C3A—C4A—H4A2 | 109.4
H4A—C4—H4B | 107.9 | H4A1—C4A—H4A2 | 108.0
N2—C5—C51 | 124.1 (6) | N2A—C5A—C51A | 126.0 (7)
N2—C5—H5 | 117.9 | N2A—C5A—H5A | 117.0
C51—C5—H5 | 117.9 | C51A—C5A—H5A | 117.0
C16—C11—C12 | 117.5 (6) | C12A—C11A—C16A | 117.2 (6)
C16—C11—C1 | 122.9 (6) | C12A—C11A—C1A | 121.5 (6)
C12—C11—C1 | 119.6 (6) | C16A—C11A—C1A | 121.3 (6)
C13—C12—C11 | 120.9 (6) | C13A—C12A—C11A | 121.8 (6)
C13—C12—H12 | 119.6 | C13A—C12A—H12A | 119.1
C11—C12—H12 | 119.6 | C11A—C12A—H12A | 119.1
C12—C13—C14 | 121.0 (6) | C12A—C13A—C14A | 121.0 (6)
C12—C13—H13 | 119.5 | C12A—C13A—H13A | 119.5
C14—C13—H13 | 119.5 | C14A—C13A—H13A | 119.5
N3—C14—C13 | 121.7 (6) | N3A—C14A—C15A | 120.5 (6)
N3—C14—C15 | 120.8 (6) | N3A—C14A—C13A | 121.9 (6)
C13—C14—C15 | 117.4 (6) | C15A—C14A—C13A | 117.7 (6)
C16—C15—C14 | 120.5 (6) | C16A—C15A—C14A | 120.6 (6)
C16—C15—H15 | 119.7 | C16A—C15A—H15A | 119.7
C14—C15—H15 | 119.7 | C14A—C15A—H15A | 119.7
C15—C16—C11 | 122.5 (6) | C15A—C16A—C11A | 121.4 (6)
C15—C16—H16 | 118.7 | C15A—C16A—H16A | 119.3
C11—C16—H16 | 118.7 | C11A—C16A—H16A | 119.3
N3—C17—H17A | 109.5 | N3A—C17A—H17D | 109.5
N3—C17—H17B | 109.5 | N3A—C17A—H17E | 109.5
H17A—C17—H17B | 109.5 | H17D—C17A—H17E | 109.5
N3—C17—H17C | 109.5 | N3A—C17A—H17F | 109.5
H17A—C17—H17C | 109.5 | H17D—C17A—H17F | 109.5
H17B—C17—H17C | 109.5 | H17E—C17A—H17F | 109.5
N3—C18—H18A | 109.5 | N3A—C18A—H18D | 109.5
N3—C18—H18B | 109.5 | N3A—C18A—H18E | 109.5
H18A—C18—H18B | 109.5 | H18D—C18A—H18E | 109.5
N3—C18—H18C | 109.5 | N3A—C18A—H18F | 109.5
H18A—C18—H18C | 109.5 | H18D—C18A—H18F | 109.5
H18B—C18—H18C | 109.5 | H18E—C18A—H18F | 109.5
C52—C51—C56 | 116.8 (6) | C56A—C51A—C52A | 117.8 (7)
C52—C51—C5 | 119.1 (7) | C56A—C51A—C5A | 122.8 (6)
C56—C51—C5 | 124.0 (6) | C52A—C51A—C5A | 119.3 (7)
C51—C52—C53 | 122.3 (8) | C53A—C52A—C51A | 122.7 (7)
C51—C52—H52 | 118.8 | C53A—C52A—H52A | 118.6
C53—C52—H52 | 118.8 | C51A—C52A—H52A | 118.7
C54—C53—C52 | 120.1 (7) | C52A—C53A—C54A | 120.4 (7)
C54—C53—H53 | 119.9 | C52A—C53A—H53A | 119.8
C52—C53—H53 | 119.9 | C54A—C53A—H53A | 119.8
C53—C54—N4 | 121.4 (7) | N4A—C54A—C53A | 120.7 (7)
C53—C54—C55 | 117.8 (7) | N4A—C54A—C55A | 121.3 (8)
N4—C54—C55 | 120.7 (7) | C53A—C54A—C55A | 118.0 (7)
C56—C55—C54 | 120.5 (7) | C54A—C55A—C56A | 120.1 (7)
C56—C55—H55 | 119.7 | C54A—C55A—H55A | 120.0
C54—C55—H55 | 119.7 | C56A—C55A—H55A | 120.0
C55—C56—C51 | 122.3 (7) | C51A—C56A—C55A | 121.0 (7)
C55—C56—H56 | 118.8 | C51A—C56A—H56A | 119.5
C51—C56—H56 | 118.8 | C55A—C56A—H56A | 119.5
N4—C57—H57A | 109.5 | N4A—C57A—H57D | 109.5
N4—C57—H57B | 109.5 | N4A—C57A—H57E | 109.5
H57A—C57—H57B | 109.5 | H57D—C57A—H57E | 109.5
N4—C57—H57C | 109.5 | N4A—C57A—H57F | 109.5
H57A—C57—H57C | 109.5 | H57D—C57A—H57F | 109.5
H57B—C57—H57C | 109.5 | H57E—C57A—H57F | 109.5
N4—C58—H58A | 109.5 | N4A—C58A—H58D | 109.5
N4—C58—H58B | 109.5 | N4A—C58A—H58E | 109.5
H58A—C58—H58B | 109.5 | H58D—C58A—H58E | 109.5
N4—C58—H58C | 109.5 | N4A—C58A—H58F | 109.5
H58A—C58—H58C | 109.5 | H58D—C58A—H58F | 109.5
H58B—C58—H58C | 109.5 | H58E—C58A—H58F | 109.5
C2—N1—C1—C11 | 178.6 (6) | C2A—N1A—C1A—C11A | 177.8 (6)
C1—N1—C2—C3 | 116.0 (7) | C1A—N1A—C2A—C3A | 117.4 (6)
N1—C2—C3—O1 | −175.3 (5) | N1A—C2A—C3A—O1A | −174.1 (5)
N1—C2—C3—C4 | 59.4 (8) | N1A—C2A—C3A—C4A | 60.4 (7)
C5—N2—C4—C3 | −128.6 (6) | C5A—N2A—C4A—C3A | −127.7 (6)
O1—C3—C4—N2 | 71.8 (7) | O1A—C3A—C4A—N2A | 71.5 (7)
C2—C3—C4—N2 | −163.0 (6) | C2A—C3A—C4A—N2A | −163.9 (5)
C4—N2—C5—C51 | 177.0 (6) | C4A—N2A—C5A—C51A | 179.9 (6)
N1—C1—C11—C16 | −2.8 (10) | N1A—C1A—C11A—C12A | 179.6 (7)
N1—C1—C11—C12 | 180.0 (7) | N1A—C1A—C11A—C16A | −0.6 (10)
C16—C11—C12—C13 | −1.7 (10) | C16A—C11A—C12A—C13A | −4.5 (10)
C1—C11—C12—C13 | 175.7 (6) | C1A—C11A—C12A—C13A | 175.3 (6)
C11—C12—C13—C14 | −1.2 (11) | C11A—C12A—C13A—C14A | 1.0 (11)
C18—N3—C14—C13 | −179.0 (7) | C17A—N3A—C14A—C15A | −178.2 (8)
C17—N3—C14—C13 | −3.1 (11) | C18A—N3A—C14A—C15A | −1.3 (11)
C18—N3—C14—C15 | 3.1 (11) | C17A—N3A—C14A—C13A | 2.2 (11)
C17—N3—C14—C15 | 178.9 (7) | C18A—N3A—C14A—C13A | 179.1 (7)
C12—C13—C14—N3 | −174.8 (7) | C12A—C13A—C14A—N3A | −177.5 (7)
C12—C13—C14—C15 | 3.2 (10) | C12A—C13A—C14A—C15A | 2.9 (10)
N3—C14—C15—C16 | 175.8 (7) | N3A—C14A—C15A—C16A | 177.2 (7)
C13—C14—C15—C16 | −2.2 (10) | C13A—C14A—C15A—C16A | −3.1 (10)
C14—C15—C16—C11 | −0.7 (10) | C14A—C15A—C16A—C11A | −0.4 (10)
C12—C11—C16—C15 | 2.7 (10) | C12A—C11A—C16A—C15A | 4.2 (10)
C1—C11—C16—C15 | −174.6 (6) | C1A—C11A—C16A—C15A | −175.6 (6)
N2—C5—C51—C52 | 169.0 (7) | N2A—C5A—C51A—C56A | −9.9 (11)
N2—C5—C51—C56 | −14.9 (11) | N2A—C5A—C51A—C52A | 173.4 (7)
C56—C51—C52—C53 | −0.3 (11) | C56A—C51A—C52A—C53A | 0.3 (10)
C5—C51—C52—C53 | 176.0 (7) | C5A—C51A—C52A—C53A | 177.1 (7)
C51—C52—C53—C54 | −1.0 (12) | C51A—C52A—C53A—C54A | −0.3 (11)
C52—C53—C54—N4 | −176.9 (7) | C57A—N4A—C54A—C53A | 8.3 (10)
C52—C53—C54—C55 | 0.7 (11) | C58A—N4A—C54A—C53A | 166.3 (7)
C58—N4—C54—C53 | −175.5 (7) | C57A—N4A—C54A—C55A | −171.8 (7)
C57—N4—C54—C53 | −2.9 (11) | C58A—N4A—C54A—C55A | −13.9 (11)
C58—N4—C54—C55 | 7.0 (12) | C52A—C53A—C54A—N4A | −179.6 (7)
C57—N4—C54—C55 | 179.6 (7) | C52A—C53A—C54A—C55A | 0.6 (11)
C53—C54—C55—C56 | 1.1 (11) | N4A—C54A—C55A—C56A | 179.4 (6)
N4—C54—C55—C56 | 178.6 (7) | C53A—C54A—C55A—C56A | −0.8 (11)
C54—C55—C56—C51 | −2.5 (12) | C52A—C51A—C56A—C55A | −0.5 (10)
C52—C51—C56—C55 | 2.1 (11) | C5A—C51A—C56A—C55A | −177.2 (6)
C5—C51—C56—C55 | −174.0 (7) | C54A—C55A—C56A—C51A | 0.8 (11)

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D—H···A | D—H | H···A | D···A | D—H···A
O1—H1···N2Ai | 0.84 (8) | 2.06 (8) | 2.889 (7) | 170 (7)
O1A—H1A···N2 | 0.84 (8) | 2.04 (8) | 2.863 (7) | 166 (7)
C57—H57B···O1ii | 0.98 | 2.53 | 3.171 (9) | 123
C57A—H57E···O1Aiii | 0.98 | 2.36 | 3.211 (8) | 145

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Figure 1.

The structure of the independent molecules A and B, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level for non-H atoms.

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Figure 2.

The structural overlay of the independent molecules A (green dashed) and B (purple) of the title compound.

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Figure 3.

Crystal packing of the title compound, indicating the O—H⋯N hydrogen bonds (dashed lines), which result in chains along the a-axis direction.

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Figure 4.

Perspective view of the molecule if the structure is refined in a cell with the a axis halved.

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Figure 5.

Partial packing diagram of the title compound with one molecule shifted by x = ½, y = 0, z = 0, showing similarities and differences between the two molecules.

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

D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A
O1—H1⋯N2A i | 0.84 (8) | 2.06 (8) | 2.889 (7) | 170 (7)
O1A—H1A⋯N2 | 0.84 (8) | 2.04 (8) | 2.863 (7) | 166 (7)
C57—H57B⋯O1ii | 0.98 | 2.53 | 3.171 (9) | 123
C57A—H57E⋯O1A iii | 0.98 | 2.36 | 3.211 (8) | 145

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

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Table 2. Experimental details

Crystal data
Chemical formula | C₂₁H₂₈N₄O
M r | 352.47
Crystal system, space group | Monoclinic, P2₁
Temperature (K) | 173
a, b, c (Å) | 9.1456 (10), 10.5860 (8), 19.974 (2)
β (°) | 97.110 (9)
V (Å³) | 1918.9 (3)
Z | 4
Radiation type | Mo Kα
μ (mm⁻¹) | 0.08
Crystal size (mm) | 0.22 × 0.03 × 0.03
Data collection
Diffractometer | STOE IPDS II two-circle
Absorption correction | Multi-scan (X-AREA; Stoe & Cie, 2001 ▸)
T min, T max | 0.426, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections | 16633, 6852, 3688
R int | 0.069
(sin θ/λ)max (Å⁻¹) | 0.609
Refinement
R[F ² > 2σ(F ²)], wR(F ²), S | 0.063, 0.156, 0.93
No. of reflections | 6852
No. of parameters | 483
No. of restraints | 1
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å⁻³) | 0.17, −0.22

Computer programs: X-AREA (Stoe & Cie, 2001 ▸), SHELXS (Sheldrick, 2008 ▸), SHELXL2014/7 (Sheldrick, 2015 ▸) and XP in SHELXTL-Plus (Sheldrick, 2008 ▸).

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