research communications
E)-benzylideneamino]propan-2-ol
of 1,3-bis[(aUniversidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No. 45-03, Bogotá, Código Postal 111321, Colombia, and bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von Laue-Str. 7, 60438 Frankfurt/Main, Germany
*Correspondence e-mail: ariverau@unal.edu.co
In the title compound, C17H18N2O, the central carbon atom with the OH substituent and one of the (E)-benzylideneamino substituents are disordered over two sets of sites with occupancies of 0.851 (4) and 0.149 (4). The relative positions of the two disorder components is equivalent to a rotation of approximately 60° about the C—N single bond. In the crystal, the molecules are held together by O—H⋯N hydrogen bonds, forming simple C(5) chains along the b-axis direction. In addition, pairs of the chains are further aggregated by weak C—H⋯π interactions.
Keywords: crystal structure; hydrogen bonding; C—H⋯π interactions; Schiff bases.
CCDC reference: 1540296
1. Chemical context
During the last decades, interest in et al. 2016; Sahu et al. 2012; Da Silva et al., 2011; Przybylski et al. 2009). The common structural feature of these compounds is the presence of a azomethine group (–R—C=N–), which can act as a hydrogen-bond acceptor or a ligand. To gain more insight into the structural and spectroscopic properties of this potentially polydentate ligand, we report herein the molecular structure of the title compound.
and their complexes has been constant due to their extensive use for industrial purposes and also for their broad range of biological activities (Al Zoubi2. Structural commentary
The molecular structure of the title compound is shown in Fig. 1. The compound exists in an E,E conformation with respect to the imine functions. One benzylideneamino segment of the molecule, C3/C4/N2/C5/C21–C26 is disordered over two sets of sites with a refined occupancy ratio of 0.851 (4):0.149 (4). The difference between the two conformers is reflected in the relative arrangement of the central spacer units. In the major disorder component, the torsion angle C3—C4—N2—C5 is −158.7 (2)° whereas the corresponding angle C3′—C4′—N2′—C5′ in the minor component is −93.3 (14)°. This translates to a rotation of approximately 60° about the C4—N2 bond. In the second, fully ordered, (E)-benzylideneamino substituent, the equivalent torsion angles C1—N1—C2—C3 and C1—N1—C2—C3′ are −102.03 (18)° and −79.8 (8)°, respectively.
Unlike some related structures, which have a well-defined synclinal (-sc) alignment of the hydroxyl and imine nitrogen atoms around the N(imine)—C—C—O(hydroxyl) bond [−65.3 (3)° (Rivera, Miranda-Carvajal, Ríos-Motta & Bolte, 2016) and −67.6 (4)° (Moodley & Van Zyl, 2012)], the orientation between these groups in the title compound differs significantly, with the N1—C2—C3—O1 and N1—C2—C3′—O1 torsion angles being 81.51 (19)° and 21.2 (14)°, respectively.
The N1=C1 and N2=C5 distances in the molecule are 1.270 (2) and 1.259 (3) Å, respectively, consistent with C=N double bonding. The C1—N1—C2 bond angle of 118.61 (15)° confirms the sp2 character of N1. The bond angles C5—N2—C4 and C5′—N2′—C4′ [116.9 (2) and 114.6 (12)°, respectively] indicate a slight loss of the sp2 character. The N1=C1 azomethine group is essentially co-planar with the attached benzene ring with an N1—C1—C11—C12 torsion angle being 2.0 (5)°. In contrast, in the disordered (E)-benzylideneamino substituent, the corresponding torsion angles N2—C5—C21—C22 and N2′—C5′—C21′—C22′ are −17.6 (6) and 21 (4)° for the major and minor disorder components, respectively. All these data suggest that the difference between these (E)-benzylideneamino substituents may result from some loss of conjugation between the phenyl ring and its azomethine substituent in the disordered branch of the molecule.
3. Supramolecular features
As found in related structures (Rivera, Miranda-Carvajal, Ríos-Motta & Bolte, 2016; Moodley & Van Zyl, 2012) in the crystal, molecules are linked by an O1—H1⋯N1 hydrogen bond, Table 1, forming columnar structures built from C(5) chains along the b-axis direction. In addition, pairs of the chains are linked by weak C24—H24⋯Cg1 interactions (Table 1 and Fig. 2), involving the C11–C16 phenyl ring, together with C15—H15⋯Cg2 and C15—H15⋯Cg3 contacts involving the phenyl rings of the two disorder components; the centroids are defined in Table 1. It is noteworthy that the shortest (and presumably the strongest) of these non-classical contacts is C15—H15⋯Cg3 involving the phenyl ring in the minor disorder component (Table 1).
4. Database survey
A search in the Cambridge Crystallographic Database (CSD Version 5.38, last update 2016; 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 et al., 2012) and 1,3-bis[(E)-(4-methoxybenzylidene)amino]propan-2-ol (Rivera, Miranda-Carvajal, Ríos-Motta & Bolte, 2016). In each of these structures, the N=C double bonds adopt E conformations.
5. Synthesis and crystallization
The title compound was prepared as described by Rivera, Miranda-Carvajal & Ríos-Motta (2016). The crude product was recrystallized from diethyl ether solution with slow evaporation of the solvent, giving colorless crystals suitable for X–ray diffraction, m.p. 396.8–398 K, yield, 40%.
6. Refinement
Crystal data, data collection and structure . The hydroxyl H atom was refined freely. All 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 and d(C—H) = 1.00 Å for C3—H3. The Uiso(H) values were constrained to 1.2Ueq(C). The C3/C4/N2/C5/C21–C26 segment of the molecule is disordered over two sets of sites with a refined occupancy ratio of 0.851 (4):0.149 (4).
details are summarized in Table 2
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Supporting information
CCDC reference: 1540296
https://doi.org/10.1107/S2056989017004741/sj5523sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017004741/sj5523Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989017004741/sj5523Isup3.cml
Data collection: X-AREA (Stoe & Cie, 2001); cell
X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS2014/7 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008).C17H18N2O | Dx = 1.211 Mg m−3 |
Mr = 266.33 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 24714 reflections |
a = 16.4313 (7) Å | θ = 2.1–25.5° |
b = 7.1909 (3) Å | µ = 0.08 mm−1 |
c = 24.7345 (11) Å | T = 173 K |
V = 2922.5 (2) Å3 | Block, colourless |
Z = 8 | 0.24 × 0.22 × 0.18 mm |
F(000) = 1136 |
STOE IPDS II two-circle diffractometer | 2200 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.054 |
ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (X-Area; Stoe & Cie, 2001) | h = −18→19 |
Tmin = 0.742, Tmax = 1.000 | k = −8→8 |
25768 measured reflections | l = −29→29 |
2574 independent reflections |
Refinement on F2 | 84 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.111 | w = 1/[σ2(Fo2) + (0.0542P)2 + 0.639P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
2574 reflections | Δρmax = 0.24 e Å−3 |
276 parameters | Δρmin = −0.21 e Å−3 |
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 | Occ. (<1) | |
O1 | 0.63353 (8) | 0.70433 (16) | 0.38320 (5) | 0.0509 (4) | |
H1 | 0.6763 (14) | 0.763 (3) | 0.3660 (9) | 0.075 (7)* | |
N1 | 0.74117 (8) | 0.41062 (18) | 0.33137 (5) | 0.0392 (3) | |
C1 | 0.73647 (10) | 0.4889 (2) | 0.28545 (6) | 0.0364 (4) | |
H1A | 0.6840 | 0.5185 | 0.2718 | 0.044* | |
C2 | 0.66704 (11) | 0.3836 (2) | 0.36223 (7) | 0.0470 (4) | |
H2A | 0.6668 | 0.2584 | 0.3789 | 0.056* | 0.851 (4) |
H2B | 0.6190 | 0.3942 | 0.3383 | 0.056* | 0.851 (4) |
H2C | 0.6278 | 0.3353 | 0.3353 | 0.056* | 0.149 (4) |
H2D | 0.6797 | 0.2768 | 0.3861 | 0.056* | 0.149 (4) |
C3 | 0.66388 (15) | 0.5357 (3) | 0.40687 (9) | 0.0350 (5) | 0.851 (4) |
H3 | 0.7194 | 0.5566 | 0.4222 | 0.042* | 0.851 (4) |
C4 | 0.60471 (12) | 0.4859 (3) | 0.45148 (8) | 0.0394 (6) | 0.851 (4) |
H4A | 0.6007 | 0.5912 | 0.4771 | 0.047* | 0.851 (4) |
H4B | 0.5501 | 0.4654 | 0.4356 | 0.047* | 0.851 (4) |
N2 | 0.62980 (16) | 0.3185 (3) | 0.48085 (10) | 0.0391 (5) | 0.851 (4) |
C5 | 0.57527 (15) | 0.2327 (3) | 0.50643 (8) | 0.0361 (5) | 0.851 (4) |
H5 | 0.5210 | 0.2773 | 0.5038 | 0.043* | 0.851 (4) |
C21 | 0.5901 (2) | 0.0675 (5) | 0.54025 (17) | 0.0352 (7) | 0.851 (4) |
C22 | 0.6613 (3) | −0.0353 (9) | 0.5350 (3) | 0.0425 (15) | 0.851 (4) |
H22 | 0.7005 | −0.0016 | 0.5085 | 0.051* | 0.851 (4) |
C23 | 0.6751 (4) | −0.1864 (10) | 0.5681 (3) | 0.0544 (14) | 0.851 (4) |
H23 | 0.7232 | −0.2582 | 0.5639 | 0.065* | 0.851 (4) |
C24 | 0.6186 (3) | −0.2338 (6) | 0.6078 (2) | 0.0561 (10) | 0.851 (4) |
H24 | 0.6295 | −0.3338 | 0.6318 | 0.067* | 0.851 (4) |
C25 | 0.5473 (3) | −0.1359 (6) | 0.61203 (15) | 0.0503 (10) | 0.851 (4) |
H25 | 0.5080 | −0.1711 | 0.6383 | 0.060* | 0.851 (4) |
C26 | 0.53203 (18) | 0.0143 (5) | 0.57820 (13) | 0.0409 (7) | 0.851 (4) |
H26 | 0.4822 | 0.0805 | 0.5809 | 0.049* | 0.851 (4) |
C11 | 0.80792 (10) | 0.5363 (2) | 0.25222 (6) | 0.0356 (4) | |
C12 | 0.88687 (10) | 0.4938 (2) | 0.26791 (7) | 0.0440 (4) | |
H12 | 0.8961 | 0.4264 | 0.3004 | 0.053* | |
C13 | 0.95204 (11) | 0.5492 (3) | 0.23646 (7) | 0.0499 (5) | |
H13 | 1.0058 | 0.5180 | 0.2472 | 0.060* | |
C14 | 0.93971 (12) | 0.6499 (2) | 0.18938 (7) | 0.0477 (4) | |
H14 | 0.9848 | 0.6897 | 0.1683 | 0.057* | |
C15 | 0.86123 (12) | 0.6919 (2) | 0.17337 (7) | 0.0474 (4) | |
H15 | 0.8522 | 0.7605 | 0.1411 | 0.057* | |
C16 | 0.79573 (11) | 0.6343 (2) | 0.20430 (6) | 0.0412 (4) | |
H16 | 0.7419 | 0.6619 | 0.1927 | 0.049* | |
C3' | 0.6215 (9) | 0.4977 (16) | 0.3939 (5) | 0.042 (3) | 0.149 (4) |
H3' | 0.5637 | 0.4580 | 0.3990 | 0.050* | 0.149 (4) |
C4' | 0.6731 (7) | 0.4957 (14) | 0.4447 (5) | 0.040 (3) | 0.149 (4) |
H4'1 | 0.7295 | 0.5323 | 0.4356 | 0.049* | 0.149 (4) |
H4'2 | 0.6512 | 0.5870 | 0.4709 | 0.049* | 0.149 (4) |
N2' | 0.6732 (9) | 0.3067 (15) | 0.4696 (4) | 0.044 (3) | 0.149 (4) |
C5' | 0.6203 (12) | 0.283 (2) | 0.5052 (6) | 0.041 (3) | 0.149 (4) |
H5' | 0.5840 | 0.3821 | 0.5129 | 0.049* | 0.149 (4) |
C21' | 0.6110 (12) | 0.104 (2) | 0.5364 (9) | 0.032 (4) | 0.149 (4) |
C22' | 0.6731 (19) | −0.025 (5) | 0.5415 (17) | 0.035 (5) | 0.149 (4) |
H22' | 0.7195 | −0.0144 | 0.5188 | 0.042* | 0.149 (4) |
C23' | 0.6693 (15) | −0.169 (5) | 0.5788 (14) | 0.039 (5) | 0.149 (4) |
H23' | 0.7164 | −0.2393 | 0.5873 | 0.047* | 0.149 (4) |
C24' | 0.5946 (13) | −0.208 (4) | 0.6038 (14) | 0.048 (6) | 0.149 (4) |
H24' | 0.5856 | −0.3222 | 0.6219 | 0.057* | 0.149 (4) |
C25' | 0.5353 (11) | −0.075 (3) | 0.6010 (8) | 0.034 (4) | 0.149 (4) |
H25' | 0.4873 | −0.0892 | 0.6221 | 0.040* | 0.149 (4) |
C26' | 0.5437 (12) | 0.079 (3) | 0.5682 (9) | 0.040 (4) | 0.149 (4) |
H26' | 0.5019 | 0.1705 | 0.5676 | 0.048* | 0.149 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0560 (8) | 0.0352 (6) | 0.0615 (8) | 0.0078 (6) | 0.0122 (6) | 0.0145 (6) |
N1 | 0.0464 (8) | 0.0304 (6) | 0.0409 (7) | −0.0005 (6) | 0.0045 (6) | 0.0015 (6) |
C1 | 0.0401 (9) | 0.0291 (7) | 0.0402 (9) | 0.0019 (6) | −0.0012 (7) | −0.0004 (6) |
C2 | 0.0511 (10) | 0.0366 (9) | 0.0534 (10) | 0.0021 (8) | 0.0146 (8) | 0.0083 (8) |
C3 | 0.0352 (12) | 0.0296 (10) | 0.0401 (12) | −0.0021 (9) | −0.0030 (10) | 0.0047 (9) |
C4 | 0.0412 (13) | 0.0369 (10) | 0.0400 (10) | 0.0021 (8) | 0.0023 (8) | 0.0030 (8) |
N2 | 0.0373 (13) | 0.0433 (11) | 0.0367 (13) | −0.0005 (10) | 0.0011 (11) | 0.0064 (9) |
C5 | 0.0352 (11) | 0.0372 (11) | 0.0360 (10) | −0.0012 (10) | −0.0007 (9) | −0.0028 (8) |
C21 | 0.0364 (18) | 0.0357 (14) | 0.0334 (15) | −0.0080 (12) | −0.0046 (13) | −0.0033 (11) |
C22 | 0.044 (2) | 0.0458 (18) | 0.038 (2) | −0.0041 (18) | −0.003 (2) | −0.0014 (17) |
C23 | 0.066 (2) | 0.044 (2) | 0.053 (3) | 0.0077 (14) | −0.0057 (16) | −0.003 (2) |
C24 | 0.068 (3) | 0.042 (2) | 0.0583 (17) | −0.0111 (18) | −0.018 (2) | 0.0112 (16) |
C25 | 0.061 (2) | 0.048 (2) | 0.0417 (15) | −0.021 (2) | −0.0047 (15) | 0.0085 (15) |
C26 | 0.0428 (13) | 0.042 (2) | 0.0376 (19) | −0.0106 (14) | −0.0008 (11) | −0.0017 (15) |
C11 | 0.0431 (9) | 0.0272 (7) | 0.0366 (8) | −0.0011 (6) | 0.0013 (7) | −0.0019 (6) |
C12 | 0.0458 (10) | 0.0428 (9) | 0.0435 (9) | −0.0006 (7) | −0.0010 (8) | 0.0081 (7) |
C13 | 0.0408 (10) | 0.0540 (11) | 0.0549 (11) | −0.0038 (8) | 0.0022 (8) | 0.0029 (9) |
C14 | 0.0540 (11) | 0.0424 (9) | 0.0468 (10) | −0.0112 (8) | 0.0105 (8) | −0.0020 (8) |
C15 | 0.0643 (12) | 0.0406 (9) | 0.0373 (9) | −0.0027 (8) | 0.0040 (8) | 0.0043 (7) |
C16 | 0.0486 (10) | 0.0374 (8) | 0.0377 (8) | 0.0034 (7) | −0.0001 (7) | 0.0005 (7) |
C3' | 0.046 (7) | 0.030 (6) | 0.050 (6) | −0.017 (5) | 0.000 (5) | 0.001 (4) |
C4' | 0.045 (7) | 0.041 (5) | 0.036 (6) | −0.007 (4) | 0.007 (5) | −0.003 (4) |
N2' | 0.048 (7) | 0.047 (5) | 0.038 (5) | −0.004 (5) | 0.001 (5) | 0.002 (4) |
C5' | 0.046 (7) | 0.040 (6) | 0.035 (6) | −0.006 (5) | −0.003 (6) | 0.000 (5) |
C21' | 0.039 (8) | 0.033 (6) | 0.024 (6) | −0.007 (5) | −0.004 (5) | −0.005 (5) |
C22' | 0.029 (7) | 0.033 (6) | 0.043 (9) | −0.007 (5) | −0.022 (6) | −0.012 (5) |
C23' | 0.036 (7) | 0.035 (8) | 0.046 (11) | 0.006 (5) | −0.014 (5) | −0.006 (8) |
C24' | 0.042 (8) | 0.029 (7) | 0.073 (13) | 0.010 (7) | −0.002 (8) | 0.011 (6) |
C25' | 0.030 (6) | 0.029 (8) | 0.042 (10) | 0.006 (5) | −0.006 (5) | 0.005 (5) |
C26' | 0.047 (7) | 0.030 (8) | 0.042 (7) | 0.003 (5) | −0.001 (5) | 0.005 (6) |
O1—C3 | 1.436 (2) | C26—H26 | 0.9500 |
O1—C3' | 1.522 (11) | C11—C12 | 1.388 (2) |
O1—H1 | 0.93 (3) | C11—C16 | 1.394 (2) |
N1—C1 | 1.270 (2) | C12—C13 | 1.382 (2) |
N1—C2 | 1.451 (2) | C12—H12 | 0.9500 |
C1—C11 | 1.473 (2) | C13—C14 | 1.386 (3) |
C1—H1A | 0.9500 | C13—H13 | 0.9500 |
C2—C3' | 1.359 (13) | C14—C15 | 1.382 (3) |
C2—C3 | 1.555 (3) | C14—H14 | 0.9500 |
C2—H2A | 0.9900 | C15—C16 | 1.384 (2) |
C2—H2B | 0.9900 | C15—H15 | 0.9500 |
C2—H2C | 0.9900 | C16—H16 | 0.9500 |
C2—H2D | 0.9900 | C3'—C4' | 1.515 (14) |
C3—C4 | 1.513 (3) | C3'—H3' | 1.0000 |
C3—H3 | 1.0000 | C4'—N2' | 1.492 (13) |
C4—N2 | 1.465 (3) | C4'—H4'1 | 0.9900 |
C4—H4A | 0.9900 | C4'—H4'2 | 0.9900 |
C4—H4B | 0.9900 | N2'—C5' | 1.249 (15) |
N2—C5 | 1.259 (3) | C5'—C21' | 1.508 (15) |
C5—C21 | 1.473 (3) | C5'—H5' | 0.9500 |
C5—H5 | 0.9500 | C21'—C26' | 1.367 (15) |
C21—C22 | 1.390 (4) | C21'—C22' | 1.382 (16) |
C21—C26 | 1.392 (4) | C22'—C23' | 1.389 (17) |
C22—C23 | 1.380 (4) | C22'—H22' | 0.9500 |
C22—H22 | 0.9500 | C23'—C24' | 1.402 (17) |
C23—C24 | 1.392 (5) | C23'—H23' | 0.9500 |
C23—H23 | 0.9500 | C24'—C25' | 1.364 (16) |
C24—C25 | 1.372 (5) | C24'—H24' | 0.9500 |
C24—H24 | 0.9500 | C25'—C26' | 1.384 (15) |
C25—C26 | 1.389 (4) | C25'—H25' | 0.9500 |
C25—H25 | 0.9500 | C26'—H26' | 0.9500 |
C3—O1—H1 | 108.2 (15) | C12—C11—C16 | 118.91 (15) |
C3'—O1—H1 | 128.8 (16) | C12—C11—C1 | 122.55 (14) |
C1—N1—C2 | 118.61 (15) | C16—C11—C1 | 118.49 (15) |
N1—C1—C11 | 123.57 (15) | C13—C12—C11 | 120.21 (16) |
N1—C1—H1A | 118.2 | C13—C12—H12 | 119.9 |
C11—C1—H1A | 118.2 | C11—C12—H12 | 119.9 |
C3'—C2—N1 | 133.2 (6) | C12—C13—C14 | 120.68 (17) |
N1—C2—C3 | 107.89 (15) | C12—C13—H13 | 119.7 |
N1—C2—H2A | 110.1 | C14—C13—H13 | 119.7 |
C3—C2—H2A | 110.1 | C15—C14—C13 | 119.42 (16) |
N1—C2—H2B | 110.1 | C15—C14—H14 | 120.3 |
C3—C2—H2B | 110.1 | C13—C14—H14 | 120.3 |
H2A—C2—H2B | 108.4 | C14—C15—C16 | 120.11 (16) |
C3'—C2—H2C | 103.9 | C14—C15—H15 | 119.9 |
N1—C2—H2C | 103.9 | C16—C15—H15 | 119.9 |
C3'—C2—H2D | 103.9 | C15—C16—C11 | 120.65 (16) |
N1—C2—H2D | 103.9 | C15—C16—H16 | 119.7 |
H2C—C2—H2D | 105.4 | C11—C16—H16 | 119.7 |
O1—C3—C4 | 105.89 (16) | C2—C3'—C4' | 99.4 (10) |
O1—C3—C2 | 108.42 (17) | C2—C3'—O1 | 114.7 (8) |
C4—C3—C2 | 111.88 (17) | C4'—C3'—O1 | 94.6 (9) |
O1—C3—H3 | 110.2 | C2—C3'—H3' | 115.1 |
C4—C3—H3 | 110.2 | C4'—C3'—H3' | 115.1 |
C2—C3—H3 | 110.2 | O1—C3'—H3' | 115.1 |
N2—C4—C3 | 112.03 (18) | N2'—C4'—C3' | 110.6 (9) |
N2—C4—H4A | 109.2 | N2'—C4'—H4'1 | 109.5 |
C3—C4—H4A | 109.2 | C3'—C4'—H4'1 | 109.5 |
N2—C4—H4B | 109.2 | N2'—C4'—H4'2 | 109.5 |
C3—C4—H4B | 109.2 | C3'—C4'—H4'2 | 109.5 |
H4A—C4—H4B | 107.9 | H4'1—C4'—H4'2 | 108.1 |
C5—N2—C4 | 116.9 (2) | C5'—N2'—C4' | 114.6 (12) |
N2—C5—C21 | 124.3 (2) | N2'—C5'—C21' | 123.3 (14) |
N2—C5—H5 | 117.9 | N2'—C5'—H5' | 118.3 |
C21—C5—H5 | 117.9 | C21'—C5'—H5' | 118.3 |
C22—C21—C26 | 119.6 (3) | C26'—C21'—C22' | 117.3 (15) |
C22—C21—C5 | 121.0 (3) | C26'—C21'—C5' | 119.1 (15) |
C26—C21—C5 | 119.4 (3) | C22'—C21'—C5' | 122.8 (16) |
C23—C22—C21 | 120.1 (4) | C21'—C22'—C23' | 122 (2) |
C23—C22—H22 | 120.0 | C21'—C22'—H22' | 119.2 |
C21—C22—H22 | 120.0 | C23'—C22'—H22' | 119.2 |
C22—C23—C24 | 120.1 (4) | C22'—C23'—C24' | 118.8 (19) |
C22—C23—H23 | 119.9 | C22'—C23'—H23' | 120.6 |
C24—C23—H23 | 119.9 | C24'—C23'—H23' | 120.6 |
C25—C24—C23 | 119.9 (3) | C25'—C24'—C23' | 117.6 (17) |
C25—C24—H24 | 120.1 | C25'—C24'—H24' | 121.2 |
C23—C24—H24 | 120.1 | C23'—C24'—H24' | 121.2 |
C24—C25—C26 | 120.5 (3) | C24'—C25'—C26' | 121.2 (16) |
C24—C25—H25 | 119.8 | C24'—C25'—H25' | 119.4 |
C26—C25—H25 | 119.8 | C26'—C25'—H25' | 119.4 |
C25—C26—C21 | 119.7 (3) | C21'—C26'—C25' | 121.4 (15) |
C25—C26—H26 | 120.1 | C21'—C26'—H26' | 119.3 |
C21—C26—H26 | 120.1 | C25'—C26'—H26' | 119.3 |
C2—N1—C1—C11 | 175.36 (14) | C1—C11—C12—C13 | −176.91 (15) |
C1—N1—C2—C3' | −79.8 (8) | C11—C12—C13—C14 | 0.9 (3) |
C1—N1—C2—C3 | −102.03 (18) | C12—C13—C14—C15 | −1.2 (3) |
N1—C2—C3—O1 | 81.51 (19) | C13—C14—C15—C16 | 0.2 (3) |
N1—C2—C3'—O1 | 21.2 (14) | C14—C15—C16—C11 | 1.1 (3) |
N1—C2—C3—C4 | −162.08 (16) | C12—C11—C16—C15 | −1.3 (2) |
O1—C3—C4—N2 | −177.91 (17) | C1—C11—C16—C15 | 176.04 (14) |
C2—C3—C4—N2 | 64.2 (2) | N1—C2—C3'—C4' | −78.4 (8) |
C3—C4—N2—C5 | −158.7 (2) | N1—C2—C3'—O1 | 21.2 (14) |
C4—N2—C5—C21 | −176.9 (3) | C2—C3'—C4'—N2' | −66.3 (11) |
N2—C5—C21—C22 | −17.6 (6) | O1—C3'—C4'—N2' | 177.7 (9) |
N2—C5—C21—C26 | 162.1 (3) | C3'—C4'—N2'—C5' | −93.3 (14) |
C26—C21—C22—C23 | −1.6 (10) | C4'—N2'—C5'—C21' | −178.5 (15) |
C5—C21—C22—C23 | 178.1 (6) | N2'—C5'—C21'—C26' | −169.5 (18) |
C21—C22—C23—C24 | −1.5 (12) | N2'—C5'—C21'—C22' | 21 (4) |
C22—C23—C24—C25 | 3.3 (11) | C26'—C21'—C22'—C23' | −3 (6) |
C23—C24—C25—C26 | −2.1 (7) | C5'—C21'—C22'—C23' | 167 (4) |
C24—C25—C26—C21 | −0.9 (5) | C21'—C22'—C23'—C24' | 14 (7) |
C22—C21—C26—C25 | 2.8 (6) | C22'—C23'—C24'—C25' | −17 (6) |
C5—C21—C26—C25 | −176.9 (3) | C23'—C24'—C25'—C26' | 10 (5) |
N1—C1—C11—C12 | 2.0 (2) | C22'—C21'—C26'—C25' | −5 (4) |
N1—C1—C11—C16 | −175.34 (15) | C5'—C21'—C26'—C25' | −174.7 (19) |
C16—C11—C12—C13 | 0.4 (2) | C24'—C25'—C26'—C21' | 1 (4) |
Cg1,Cg2, and Cg3, are the centroids of the C11–C16, C21–C26 and C21'–C26' rings, respectively |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.93 (3) | 1.92 (3) | 2.8430 (19) | 174 (2) |
C24—H24···Cg1ii | 0.95 | 2.88 | 3.802 (5) | 164 |
C15—H15···Cg2iii | 0.95 | 2.96 | 3.796 (3) | 148 |
C15—H15···Cg3iii | 0.95 | 2.79 | 3.640 (12) | 150 |
Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+3/2, −y, z+1/2; (iii) −x+3/2, −y+1, z−1/2. |
Acknowledgements
IMC is grateful to COLCIENCIAS for his doctoral scholarship.
Funding information
Funding for this research was provided by: Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia (award No. 35816).
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