research communications
1,3-Bis{(E)-[4-(dimethylamino)benzylidene]amino}propan-2-ol: chain structure formation via an O—H⋯N hydrogen bond
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
The 21H28N4O, 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 and the benzene ring. In the O—H⋯N hydrogen bonds together with C—H⋯O hydrogen bonds link neighbouring supramolecular dimers into a three-dimensional network.
of the title compound, CCCDC reference: 1547455
1. Chemical context
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 of the title compound is reported here.
play important roles in the development of coordination chemistry related to catalysis, enzymatic reactions, and supramolecular architectures. Crystal structures of derived from substituted benzaldehydes and 1,3-diaminopropan-2-ol have been reported earlier (Azam, Warad, Al-Resayes2. Structural commentary
The title compound crystallizes with two unique molecules in the 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.
The conformers, labeledBond 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 of the N4A atom may not be completely conjugated with the benzene ring (C51A–C56A).
3. 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⋯O1Aiii hydrogen bonds (Table 1).
4. 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.
5. 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%).
6. Refinement
Crystal data, data collection and structure . The coordinates of the hydroxyl H atom were refined with Uiso(H) = 1.5Ueq(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 Uiso(H) values were constrained to 1.5Ueq(Cmethyl) or 1.2Ueq(C) for the remaining H atoms. The structure shows signs of a 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 with two molecules in the asymmetric unit.
details are summarized in Table 2Supporting information
CCDC reference: 1547455
https://doi.org/10.1107/S2056989017006429/sj5528sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017006429/sj5528Isup2.hkl
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: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015).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 |
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 |
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 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.2650 (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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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 |
Symmetry codes: (i) x−1, y, z; (ii) −x, y−1/2, −z; (iii) −x+1, y−1/2, −z. |
Acknowledgements
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.
References
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