research communications
Two polymorphs of N,N′-diphenyl-2-[1-(propylamino)ethylidene]propanediamide
aInstitut für Anorganische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Str. 29, 09599 Freiberg, Germany
*Correspondence e-mail: uwe.boehme@chemie.tu-freiberg.de
Two polymorphs of the title compound, C20H23N3O2, have been isolated. Polymorph (I) crystallizes in the monoclinic P21/n and polymorph (II) in the tetragonal I41/a. The main difference between the two polymorphs on the molecular level is the orientation of the n-propyl group. This group is antiperiplanar in (I) and synclinal in (II). The core of the molecule consists of two carbamoyl units bound to an enamine unit. The most prominent features are intramolecular N—H⋯O hydrogen bonds in both polymorphs. Both polymorphs form dimers with graph set R22(12) via intermolecular N—H⋯O hydrogen bonds. Adjacent dimers of (I) are connected via a weak C—H⋯O interaction, resulting in a chain parallel to the crystallographic a-axis. The dimers of (II) are connected by weak C—H⋯π interactions, forming intermolecular chains along the c-axis direction.
Keywords: crystal structure; polymorph; enamine; push–pull alkene.
1. Chemical context
N,N′-Diphenyl-2-[1-(propylamino)ethylidene]propanediamide is an insertion product from an enamine and phenyl isocyanate. This was obtained in our work with different types of silicon–nitrogen compounds (Herbig et al., 2019a, 2021, 2022). The Si—N bonds can be subjected to insertion of different heteroallenes such as CO2 and isocyanates (Kraushaar et al., 2012, 2014, 2017; Herbig et al., 2018, 2019b). Insertion reactions into silicon-substituted were investigated as a continuation of our research in this area.
2. Structural commentary
Two polymorphs of the title compound were obtained from a single reaction batch. Polymorph (I) crystallizes in the monoclinic P21/n, polymorph (II) in the tetragonal I41/a. The main difference between the polymorphs on the molecular level is the orientation of the n-propyl group. This group is antiperiplanar in (I) and synclinal in (II), as can be seen from the values of the torsion angles C1—C2—C3—N1 (see Tables 1, 2 and Figs. 1, 2). The n-propyl group with C1—C2—C3 is disordered in (II), with site occupancies of 0.794 (7) and 0.206 (7) for parts A and B, respectively.
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The double bond between C4 and C5 is slightly elongated [1.400 (2) and 1.394 (3) Å], but not as strongly as in the push–pull N,N′-acetals, which have values of 1.45 to 1.47 Å (Ye et al., 2010). The carbamoyl units are characterized by C=O double bonds and shortened C—N bonds (Tables 1 and 2), the latter having values between 1.360 (2) to 1.369 (3) Å, whereas the sum of covalent radii of C and N is 1.472 Å (Pauling, 1962).
from cyclic ketene-The core of the molecule consists of two carbamoyl units (N2—C7—O1 and N3—C14—O2) bound to an enamine unit (C5—C4—N1). These planar units span certain dihedral angles between each other. The dihedral angles are listed in Table 3. The dihedral angle between N1—C4—C5 and N3—C14—O2 is small in both polymorphs, with values of 10.1 (4)° in (I) and 8.0 (3)° in (II). The dihedral angles between plane N1—C4—C5 and plane N2—C7—O1 adopt larger values of 49.0 (2)° in (I) and 51.5 (2)° in (II). This means that the carbamoyl unit N2—C7—O1 is rotated further away from the enamine group than the other carbamoyl unit. Small differences between both polymorphs are found in the orientation of the phenyl groups relative to the carbamoyl units (see Table 3).
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There are several intramolecular hydrogen bonds in (I) and (II). The interactions N1—H1N⋯O2 and N3—H3N⋯O1 feature H⋯O distances below 2 Å (see Tables 4 and 5), which qualifies these as hydrogen bonds of moderate strength (Gilli & Gilli, 2009). Further intramolecular interactions are present between C6—H6B⋯N2, C13—H13⋯O1, and C20—H20⋯O2 in both polymorphs.
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3. Supramolecular features
The density of (I) is 1.243 and of (II) 1.235 Mg m−3. The molecular arrangement is different in both crystals because of the crystal symmetry. The 21 screw axes running parallel to the b-axis in the monoclinic crystal (I) lead to a parallel arrangement of molecules in the In contrast, in the tetragonal crystal of (II), the molecules are grouped around the 41 screw axes running parallel to the c-axis. This leads to pairs of molecules that are oriented at an angle of 90° to each other. In (I) and (II), these dimers are formed by the intermolecular N2—H2N⋯O2 hydrogen bonds, described by graph set R22(12) (see Fig. 3). Adjacent dimers are connected by a weak C10—H10⋯O1 interaction, resulting in a chain along the crystallographic a-axis direction in (I) (Fig. 4). In (II), these dimers are connected not via this C—H⋯O contact, but by weak C—H⋯π interactions, forming intermolecular chains along the c-axis direction (Fig. 5). The latter are also observed in (I).
4. Database survey
Related structures are 2,2′-[benzylidenemethylenebis(carbonylamino)]dibenzoic acid (Taga et al., 1985), bis(N,N-diphenyl)(m-chlorobenzylidene)malonyldiamide (Kerr et al., 1985; CSD refode: FACDES) and 1,1-bis(N-phenylcarbamoyl)-2-(p-chlorophenyl)ethylene (Kerr & Ashmore, 1973; CSD refode: PCMETY). Furthermore, several related push–pull from cyclic ketene-N,N′-acetals have been prepared and structurally characterized (Ye et al., 2010). Therein, the push–pull effect reduces the double-bond order by intramolecular charge transfer. This makes such interesting as substrates for second order non-linear optical materials.
5. Synthesis and crystallization
N,N′-Diphenyl-2-[1-(propylamino)ethylidene]propanediamide was obtained from the reaction of a silylated enamine (N-propyl-N-trimethylsilylprop-1-en-2-amine) and phenyl isocyanate. As shown in Fig. 6, insertion of Ph-NCO into both C—H bonds of the enamine takes place. This reaction is possible due to the lability of the β-hydrogen atoms of the enamine (Ozaki, 1972). Traces of water lead to the cleavage of the Si—N bond from the intermediate to yield the title compound.
To a solution of 0.46 g (3 mmol) N-propyl-N-trimethylsilylprop-1-en-2-amine in 10 mL of n-pentane was added dropwise 0.60 g (5 mmol) of phenylisocyanate at 273 K. After standing three days at room temperature, some crystals suitable for single-crystal X-ray diffraction were obtained. The polymorphs were recognised by their different crystal shapes: (I) forms small prisms, (II) forms large flat prisms. Both are colourless.
NMR spectroscopy showed that the batch product is a mixture of many components. Further purification of the product mixture was not successful.
6. Refinement
Crystal data, data collection and structure . Hydrogen atoms bonded to C were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95 Å for H(Ph), 0.99 for CH2, and 0.98 Å for CH3. Uiso(H) = xUeq(C), where x = 1.2 for H(Ph) and CH2, and 1.5 for CH3. Hydrogen atoms on nitrogen were localized from residual electron-density maps and were freely refined.
details are summarized in Table 6
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Supporting information
https://doi.org/10.1107/S2056989023002141/pk2679sup1.cif
contains datablocks I, II, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023002141/pk2679Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989023002141/pk2679IIsup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989023002141/pk2679Isup4.cml
For both structures, data collection: X-AREA (Stoe, 2009); cell
X-AREA (Stoe, 2009); data reduction: X-RED (Stoe, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).C20H23N3O2 | F(000) = 720 |
Mr = 337.41 | Dx = 1.243 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3881 (4) Å | Cell parameters from 18377 reflections |
b = 24.3653 (9) Å | θ = 2.3–27.4° |
c = 9.2614 (5) Å | µ = 0.08 mm−1 |
β = 107.724 (4)° | T = 193 K |
V = 1802.99 (15) Å3 | Prism, colourless |
Z = 4 | 0.48 × 0.21 × 0.18 mm |
Stoe IPDS 2 diffractometer | 3882 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2967 reflections with I > 2σ(I) |
Detector resolution: 6.67 pixels mm-1 | Rint = 0.054 |
rotation method scans | θmax = 27.0°, θmin = 2.5° |
Absorption correction: integration (X-RED; Stoe, 2009) | h = −10→10 |
Tmin = 0.820, Tmax = 0.980 | k = −30→31 |
18377 measured reflections | l = −11→11 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0475P)2 + 0.6249P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max = 0.001 |
3882 reflections | Δρmax = 0.14 e Å−3 |
240 parameters | Δρmin = −0.23 e Å−3 |
0 restraints |
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 | ||
C1 | 0.1490 (3) | 1.22813 (9) | 0.6450 (3) | 0.0565 (6) | |
H1A | 0.059051 | 1.234402 | 0.690216 | 0.085* | |
H1B | 0.138400 | 1.254351 | 0.562369 | 0.085* | |
H1C | 0.257591 | 1.233135 | 0.722392 | 0.085* | |
C2 | 0.1367 (3) | 1.17012 (8) | 0.5832 (2) | 0.0457 (5) | |
H2A | 0.034581 | 1.166745 | 0.495147 | 0.055* | |
H2B | 0.234587 | 1.162517 | 0.547866 | 0.055* | |
C3 | 0.1304 (2) | 1.12830 (7) | 0.7020 (2) | 0.0363 (4) | |
H3A | 0.220902 | 1.135805 | 0.797292 | 0.044* | |
H3B | 0.021949 | 1.131048 | 0.723328 | 0.044* | |
N1 | 0.15026 (19) | 1.07318 (6) | 0.64863 (18) | 0.0342 (3) | |
H1N | 0.187 (3) | 1.0698 (10) | 0.567 (3) | 0.050 (6)* | |
C4 | 0.1460 (2) | 1.02613 (7) | 0.72048 (19) | 0.0311 (4) | |
C5 | 0.1863 (2) | 0.97588 (7) | 0.66711 (19) | 0.0297 (4) | |
C6 | 0.1047 (2) | 1.03163 (8) | 0.8671 (2) | 0.0399 (4) | |
H6A | 0.175144 | 1.060165 | 0.929658 | 0.060* | |
H6B | 0.125317 | 0.996585 | 0.921533 | 0.060* | |
H6C | −0.013406 | 1.041718 | 0.845375 | 0.060* | |
C7 | 0.1491 (2) | 0.92312 (7) | 0.72906 (19) | 0.0311 (4) | |
O1 | 0.24257 (16) | 0.88268 (6) | 0.75027 (15) | 0.0413 (3) | |
N2 | −0.00388 (19) | 0.92087 (6) | 0.75185 (18) | 0.0336 (3) | |
H2N | −0.073 (3) | 0.9468 (10) | 0.708 (3) | 0.049 (6)* | |
C8 | −0.0758 (2) | 0.87725 (7) | 0.81029 (19) | 0.0311 (4) | |
C9 | −0.2493 (2) | 0.87627 (8) | 0.7747 (2) | 0.0362 (4) | |
H9 | −0.314313 | 0.903796 | 0.710646 | 0.043* | |
C10 | −0.3278 (2) | 0.83562 (8) | 0.8319 (2) | 0.0416 (4) | |
H10 | −0.446393 | 0.835127 | 0.806474 | 0.050* | |
C11 | −0.2340 (3) | 0.79569 (8) | 0.9259 (2) | 0.0448 (5) | |
H11 | −0.287648 | 0.767829 | 0.965915 | 0.054* | |
C12 | −0.0622 (3) | 0.79650 (9) | 0.9612 (2) | 0.0452 (5) | |
H12 | 0.002335 | 0.769047 | 1.025872 | 0.054* | |
C13 | 0.0176 (2) | 0.83696 (8) | 0.9033 (2) | 0.0390 (4) | |
H13 | 0.136133 | 0.836958 | 0.927613 | 0.047* | |
C14 | 0.25399 (19) | 0.97405 (7) | 0.53946 (19) | 0.0299 (4) | |
O2 | 0.25269 (15) | 1.01470 (5) | 0.45613 (14) | 0.0342 (3) | |
N3 | 0.3185 (2) | 0.92538 (7) | 0.51188 (18) | 0.0359 (4) | |
H3N | 0.313 (3) | 0.8986 (9) | 0.576 (2) | 0.041 (6)* | |
C15 | 0.3593 (2) | 0.90910 (8) | 0.3819 (2) | 0.0333 (4) | |
C16 | 0.3682 (2) | 0.85294 (9) | 0.3598 (2) | 0.0425 (5) | |
H16 | 0.347921 | 0.828183 | 0.431518 | 0.051* | |
C17 | 0.4061 (3) | 0.83256 (10) | 0.2347 (2) | 0.0498 (5) | |
H17 | 0.412200 | 0.794052 | 0.221270 | 0.060* | |
C18 | 0.4352 (2) | 0.86814 (10) | 0.1293 (2) | 0.0485 (5) | |
H18 | 0.459997 | 0.854333 | 0.042642 | 0.058* | |
C19 | 0.4277 (2) | 0.92404 (10) | 0.1514 (2) | 0.0465 (5) | |
H19 | 0.447291 | 0.948603 | 0.078995 | 0.056* | |
C20 | 0.3919 (2) | 0.94502 (8) | 0.2779 (2) | 0.0395 (4) | |
H20 | 0.389836 | 0.983552 | 0.292900 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0671 (15) | 0.0358 (11) | 0.0656 (15) | 0.0032 (10) | 0.0187 (12) | 0.0015 (10) |
C2 | 0.0514 (12) | 0.0372 (11) | 0.0476 (11) | 0.0013 (9) | 0.0140 (9) | −0.0014 (9) |
C3 | 0.0352 (9) | 0.0313 (9) | 0.0425 (10) | 0.0012 (7) | 0.0122 (8) | −0.0075 (8) |
N1 | 0.0357 (8) | 0.0317 (8) | 0.0375 (8) | 0.0006 (6) | 0.0142 (7) | −0.0033 (6) |
C4 | 0.0251 (8) | 0.0352 (9) | 0.0332 (9) | −0.0010 (7) | 0.0094 (7) | −0.0017 (7) |
C5 | 0.0267 (8) | 0.0323 (9) | 0.0310 (8) | 0.0009 (6) | 0.0103 (7) | 0.0006 (7) |
C6 | 0.0433 (10) | 0.0433 (11) | 0.0375 (10) | 0.0001 (8) | 0.0186 (8) | −0.0047 (8) |
C7 | 0.0289 (8) | 0.0357 (9) | 0.0298 (8) | 0.0020 (7) | 0.0106 (7) | 0.0011 (7) |
O1 | 0.0395 (7) | 0.0422 (8) | 0.0472 (8) | 0.0115 (6) | 0.0210 (6) | 0.0118 (6) |
N2 | 0.0292 (7) | 0.0316 (8) | 0.0418 (8) | 0.0020 (6) | 0.0137 (6) | 0.0064 (7) |
C8 | 0.0342 (9) | 0.0313 (9) | 0.0304 (8) | −0.0012 (7) | 0.0137 (7) | −0.0011 (7) |
C9 | 0.0334 (9) | 0.0385 (10) | 0.0389 (10) | 0.0008 (7) | 0.0143 (8) | 0.0017 (8) |
C10 | 0.0353 (10) | 0.0450 (11) | 0.0485 (11) | −0.0043 (8) | 0.0186 (8) | −0.0006 (9) |
C11 | 0.0471 (11) | 0.0396 (11) | 0.0529 (12) | −0.0077 (9) | 0.0228 (9) | 0.0053 (9) |
C12 | 0.0451 (11) | 0.0403 (11) | 0.0505 (12) | 0.0015 (8) | 0.0150 (9) | 0.0117 (9) |
C13 | 0.0329 (9) | 0.0402 (10) | 0.0432 (10) | −0.0001 (8) | 0.0106 (8) | 0.0070 (8) |
C14 | 0.0233 (7) | 0.0337 (9) | 0.0326 (9) | 0.0006 (6) | 0.0080 (6) | 0.0011 (7) |
O2 | 0.0344 (6) | 0.0347 (7) | 0.0373 (7) | 0.0029 (5) | 0.0165 (5) | 0.0046 (5) |
N3 | 0.0414 (8) | 0.0329 (8) | 0.0393 (8) | 0.0073 (7) | 0.0210 (7) | 0.0036 (7) |
C15 | 0.0255 (8) | 0.0406 (10) | 0.0352 (9) | 0.0045 (7) | 0.0115 (7) | −0.0016 (7) |
C16 | 0.0421 (10) | 0.0425 (11) | 0.0459 (11) | 0.0077 (8) | 0.0180 (9) | −0.0017 (9) |
C17 | 0.0481 (12) | 0.0524 (13) | 0.0495 (12) | 0.0083 (9) | 0.0158 (9) | −0.0144 (10) |
C18 | 0.0359 (10) | 0.0712 (15) | 0.0390 (10) | 0.0057 (10) | 0.0124 (8) | −0.0138 (10) |
C19 | 0.0372 (10) | 0.0668 (14) | 0.0397 (11) | 0.0019 (9) | 0.0181 (8) | 0.0006 (10) |
C20 | 0.0354 (10) | 0.0450 (11) | 0.0431 (10) | 0.0026 (8) | 0.0193 (8) | −0.0001 (8) |
C1—C2 | 1.517 (3) | C9—C10 | 1.381 (3) |
C1—H1A | 0.9800 | C9—H9 | 0.9500 |
C1—H1B | 0.9800 | C10—C11 | 1.381 (3) |
C1—H1C | 0.9800 | C10—H10 | 0.9500 |
C2—C3 | 1.512 (3) | C11—C12 | 1.377 (3) |
C2—H2A | 0.9900 | C11—H11 | 0.9500 |
C2—H2B | 0.9900 | C12—C13 | 1.388 (3) |
C3—N1 | 1.458 (2) | C12—H12 | 0.9500 |
C3—H3A | 0.9900 | C13—H13 | 0.9500 |
C3—H3B | 0.9900 | C14—O2 | 1.254 (2) |
N1—C4 | 1.331 (2) | C14—N3 | 1.360 (2) |
N1—H1N | 0.90 (2) | N3—C15 | 1.405 (2) |
C4—C5 | 1.400 (2) | N3—H3N | 0.89 (2) |
C4—C6 | 1.506 (2) | C15—C20 | 1.389 (3) |
C5—C14 | 1.460 (2) | C15—C16 | 1.389 (3) |
C5—C7 | 1.479 (2) | C16—C17 | 1.384 (3) |
C6—H6A | 0.9800 | C16—H16 | 0.9500 |
C6—H6B | 0.9800 | C17—C18 | 1.381 (3) |
C6—H6C | 0.9800 | C17—H17 | 0.9500 |
C7—O1 | 1.237 (2) | C18—C19 | 1.382 (3) |
C7—N2 | 1.364 (2) | C18—H18 | 0.9500 |
N2—C8 | 1.409 (2) | C19—C20 | 1.392 (3) |
N2—H2N | 0.87 (2) | C19—H19 | 0.9500 |
C8—C13 | 1.382 (3) | C20—H20 | 0.9500 |
C8—C9 | 1.391 (2) | ||
C2—C1—H1A | 109.5 | C9—C8—N2 | 117.48 (16) |
C2—C1—H1B | 109.5 | C10—C9—C8 | 120.55 (18) |
H1A—C1—H1B | 109.5 | C10—C9—H9 | 119.7 |
C2—C1—H1C | 109.5 | C8—C9—H9 | 119.7 |
H1A—C1—H1C | 109.5 | C11—C10—C9 | 120.02 (18) |
H1B—C1—H1C | 109.5 | C11—C10—H10 | 120.0 |
C3—C2—C1 | 111.53 (18) | C9—C10—H10 | 120.0 |
C3—C2—H2A | 109.3 | C12—C11—C10 | 119.58 (18) |
C1—C2—H2A | 109.3 | C12—C11—H11 | 120.2 |
C3—C2—H2B | 109.3 | C10—C11—H11 | 120.2 |
C1—C2—H2B | 109.3 | C11—C12—C13 | 120.78 (19) |
H2A—C2—H2B | 108.0 | C11—C12—H12 | 119.6 |
N1—C3—C2 | 109.93 (15) | C13—C12—H12 | 119.6 |
N1—C3—H3A | 109.7 | C8—C13—C12 | 119.77 (18) |
C2—C3—H3A | 109.7 | C8—C13—H13 | 120.1 |
N1—C3—H3B | 109.7 | C12—C13—H13 | 120.1 |
C2—C3—H3B | 109.7 | O2—C14—N3 | 120.18 (15) |
H3A—C3—H3B | 108.2 | O2—C14—C5 | 122.81 (16) |
C4—N1—C3 | 126.89 (16) | N3—C14—C5 | 117.00 (15) |
C4—N1—H1N | 114.0 (15) | C14—N3—C15 | 128.45 (16) |
C3—N1—H1N | 118.2 (15) | C14—N3—H3N | 114.1 (14) |
N1—C4—C5 | 122.05 (16) | C15—N3—H3N | 116.0 (14) |
N1—C4—C6 | 114.99 (16) | C20—C15—C16 | 119.20 (17) |
C5—C4—C6 | 122.87 (16) | C20—C15—N3 | 124.55 (17) |
C4—C5—C14 | 120.53 (15) | C16—C15—N3 | 116.25 (17) |
C4—C5—C7 | 121.41 (15) | C17—C16—C15 | 120.9 (2) |
C14—C5—C7 | 117.88 (15) | C17—C16—H16 | 119.6 |
C4—C6—H6A | 109.5 | C15—C16—H16 | 119.6 |
C4—C6—H6B | 109.5 | C18—C17—C16 | 120.1 (2) |
H6A—C6—H6B | 109.5 | C18—C17—H17 | 119.9 |
C4—C6—H6C | 109.5 | C16—C17—H17 | 119.9 |
H6A—C6—H6C | 109.5 | C17—C18—C19 | 119.21 (19) |
H6B—C6—H6C | 109.5 | C17—C18—H18 | 120.4 |
O1—C7—N2 | 121.60 (16) | C19—C18—H18 | 120.4 |
O1—C7—C5 | 123.75 (15) | C18—C19—C20 | 121.2 (2) |
N2—C7—C5 | 114.50 (15) | C18—C19—H19 | 119.4 |
C7—N2—C8 | 128.54 (16) | C20—C19—H19 | 119.4 |
C7—N2—H2N | 115.0 (15) | C15—C20—C19 | 119.38 (19) |
C8—N2—H2N | 115.2 (15) | C15—C20—H20 | 120.3 |
C13—C8—C9 | 119.29 (17) | C19—C20—H20 | 120.3 |
C13—C8—N2 | 123.20 (16) | ||
C1—C2—C3—N1 | −169.39 (17) | C10—C11—C12—C13 | 0.0 (3) |
C2—C3—N1—C4 | −177.75 (17) | C9—C8—C13—C12 | −0.6 (3) |
C3—N1—C4—C5 | −172.23 (16) | N2—C8—C13—C12 | 177.48 (18) |
C3—N1—C4—C6 | 4.4 (3) | C11—C12—C13—C8 | 0.6 (3) |
N1—C4—C5—C14 | 7.3 (3) | C4—C5—C14—O2 | −12.5 (3) |
C6—C4—C5—C14 | −169.03 (16) | C7—C5—C14—O2 | 162.54 (15) |
N1—C4—C5—C7 | −167.58 (16) | C4—C5—C14—N3 | 168.22 (15) |
C6—C4—C5—C7 | 16.1 (2) | C7—C5—C14—N3 | −16.7 (2) |
C4—C5—C7—O1 | −142.19 (18) | O2—C14—N3—C15 | −13.5 (3) |
C14—C5—C7—O1 | 42.8 (2) | C5—C14—N3—C15 | 165.78 (17) |
C4—C5—C7—N2 | 42.2 (2) | C14—N3—C15—C20 | 22.0 (3) |
C14—C5—C7—N2 | −132.82 (16) | C14—N3—C15—C16 | −158.64 (18) |
O1—C7—N2—C8 | 5.0 (3) | C20—C15—C16—C17 | −1.1 (3) |
C5—C7—N2—C8 | −179.29 (16) | N3—C15—C16—C17 | 179.48 (18) |
C7—N2—C8—C13 | 24.0 (3) | C15—C16—C17—C18 | −0.3 (3) |
C7—N2—C8—C9 | −157.83 (18) | C16—C17—C18—C19 | 0.7 (3) |
C13—C8—C9—C10 | 0.1 (3) | C17—C18—C19—C20 | 0.2 (3) |
N2—C8—C9—C10 | −178.08 (17) | C16—C15—C20—C19 | 2.0 (3) |
C8—C9—C10—C11 | 0.4 (3) | N3—C15—C20—C19 | −178.67 (17) |
C9—C10—C11—C12 | −0.5 (3) | C18—C19—C20—C15 | −1.5 (3) |
Cg2 is the centroid of the C15–C20 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2 | 0.90 (2) | 1.87 (2) | 2.623 (2) | 139 (2) |
N3—H3N···O1 | 0.89 (2) | 1.92 (2) | 2.687 (2) | 142.9 (19) |
C6—H6B···N2 | 0.98 | 2.45 | 2.943 (3) | 111 |
C13—H13···O1 | 0.95 | 2.37 | 2.905 (2) | 115 |
C20—H20···O2 | 0.95 | 2.29 | 2.854 (2) | 117 |
N2—H2N···O2i | 0.87 (2) | 2.02 (2) | 2.843 (2) | 158 (2) |
C10—H10···O1ii | 0.95 | 2.76 | 3.635 (2) | 154 |
C13—H13···Cg2iii | 0.95 | 3.40 | 4.011 (2) | 124 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x−1, y, z; (iii) x, y, z+1. |
C20H23N3O2 | Dx = 1.235 Mg m−3 |
Mr = 337.41 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, I41/a | Cell parameters from 23893 reflections |
a = 27.7071 (11) Å | θ = 2.7–27.2° |
c = 9.4575 (4) Å | µ = 0.08 mm−1 |
V = 7260.4 (7) Å3 | T = 193 K |
Z = 16 | Prism, colourless |
F(000) = 2880 | 0.49 × 0.35 × 0.25 mm |
Stoe IPDS 2T diffractometer | 3884 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2635 reflections with I > 2σ(I) |
Detector resolution: 6.67 pixels mm-1 | Rint = 0.042 |
rotation method scans | θmax = 26.9°, θmin = 2.7° |
Absorption correction: integration (X-RED; Stoe, 2009) | h = −34→30 |
Tmin = 0.844, Tmax = 0.980 | k = −34→35 |
23893 measured reflections | l = −12→11 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0409P)2 + 6.4556P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
3884 reflections | Δρmax = 0.25 e Å−3 |
269 parameters | Δρmin = −0.18 e Å−3 |
69 restraints |
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) | |
C1A | 0.33034 (19) | 0.4509 (2) | 1.0073 (5) | 0.1009 (15) | 0.794 (7) |
H1A | 0.345612 | 0.480495 | 1.042488 | 0.151* | 0.794 (7) |
H1B | 0.315992 | 0.433244 | 1.086538 | 0.151* | 0.794 (7) |
H1C | 0.305092 | 0.459356 | 0.939020 | 0.151* | 0.794 (7) |
C2A | 0.36613 (16) | 0.42112 (13) | 0.9393 (4) | 0.0792 (12) | 0.794 (7) |
H2A | 0.349729 | 0.392523 | 0.898911 | 0.095* | 0.794 (7) |
H2B | 0.388915 | 0.409434 | 1.012267 | 0.095* | 0.794 (7) |
C3A | 0.39475 (11) | 0.44513 (12) | 0.8236 (4) | 0.0557 (9) | 0.794 (7) |
H3A | 0.416173 | 0.421327 | 0.777213 | 0.067* | 0.794 (7) |
H3B | 0.372703 | 0.458651 | 0.751383 | 0.067* | 0.794 (7) |
C1B | 0.3142 (5) | 0.4689 (5) | 0.9652 (16) | 0.064 (4) | 0.206 (7) |
H1D | 0.335316 | 0.489802 | 1.021394 | 0.095* | 0.206 (7) |
H1E | 0.294887 | 0.448625 | 1.028587 | 0.095* | 0.206 (7) |
H1F | 0.292641 | 0.488873 | 0.907398 | 0.095* | 0.206 (7) |
C2B | 0.3429 (5) | 0.4388 (5) | 0.8749 (18) | 0.082 (4) | 0.206 (7) |
H2C | 0.334739 | 0.448684 | 0.777208 | 0.098* | 0.206 (7) |
H2D | 0.329972 | 0.405792 | 0.886790 | 0.098* | 0.206 (7) |
C3B | 0.3960 (4) | 0.4337 (4) | 0.8773 (17) | 0.060 (4) | 0.206 (7) |
H3C | 0.406400 | 0.416664 | 0.790496 | 0.072* | 0.206 (7) |
H3D | 0.405204 | 0.413461 | 0.959305 | 0.072* | 0.206 (7) |
N1 | 0.42335 (7) | 0.48356 (7) | 0.8871 (2) | 0.0554 (5) | |
H1N | 0.4203 (8) | 0.4899 (8) | 0.981 (3) | 0.062 (7)* | |
C4 | 0.45371 (7) | 0.51141 (7) | 0.8148 (2) | 0.0489 (5) | |
C5 | 0.47728 (7) | 0.55038 (7) | 0.8774 (2) | 0.0441 (4) | |
C6 | 0.45777 (9) | 0.50023 (10) | 0.6592 (2) | 0.0673 (6) | |
H6A | 0.474937 | 0.469611 | 0.646512 | 0.101* | |
H6B | 0.475621 | 0.526138 | 0.611807 | 0.101* | |
H6C | 0.425402 | 0.497686 | 0.618089 | 0.101* | |
C7 | 0.51595 (8) | 0.57654 (7) | 0.8002 (2) | 0.0503 (5) | |
O1 | 0.51926 (7) | 0.62093 (5) | 0.79818 (17) | 0.0724 (5) | |
N2 | 0.54997 (6) | 0.54761 (6) | 0.73837 (19) | 0.0496 (4) | |
H2N | 0.5496 (8) | 0.5170 (8) | 0.764 (2) | 0.055 (6)* | |
C8 | 0.59020 (8) | 0.56177 (7) | 0.6563 (2) | 0.0486 (5) | |
C9 | 0.62718 (8) | 0.52880 (9) | 0.6397 (2) | 0.0607 (6) | |
H9 | 0.625036 | 0.497964 | 0.683170 | 0.073* | |
C10 | 0.66752 (9) | 0.54064 (11) | 0.5594 (3) | 0.0747 (7) | |
H10 | 0.692931 | 0.517901 | 0.548843 | 0.090* | |
C11 | 0.67088 (10) | 0.58508 (11) | 0.4952 (3) | 0.0752 (7) | |
H11 | 0.698696 | 0.593338 | 0.441738 | 0.090* | |
C12 | 0.63374 (11) | 0.61724 (9) | 0.5093 (3) | 0.0758 (8) | |
H12 | 0.635694 | 0.647678 | 0.463431 | 0.091* | |
C13 | 0.59336 (10) | 0.60625 (8) | 0.5892 (3) | 0.0660 (6) | |
H13 | 0.567914 | 0.629032 | 0.598067 | 0.079* | |
C14 | 0.46565 (7) | 0.56580 (6) | 1.0214 (2) | 0.0409 (4) | |
O2 | 0.43901 (5) | 0.54185 (4) | 1.10290 (14) | 0.0463 (3) | |
N3 | 0.48566 (6) | 0.60834 (6) | 1.06502 (18) | 0.0480 (4) | |
H3N | 0.5014 (9) | 0.6240 (9) | 0.996 (3) | 0.069 (7)* | |
C15 | 0.48675 (7) | 0.62908 (7) | 1.2011 (2) | 0.0441 (4) | |
C16 | 0.51880 (8) | 0.66737 (7) | 1.2202 (2) | 0.0539 (5) | |
H16 | 0.538506 | 0.677647 | 1.143708 | 0.065* | |
C17 | 0.52215 (9) | 0.69048 (8) | 1.3491 (3) | 0.0652 (6) | |
H17 | 0.543793 | 0.716791 | 1.360352 | 0.078* | |
C18 | 0.49444 (10) | 0.67569 (9) | 1.4611 (3) | 0.0726 (7) | |
H18 | 0.496925 | 0.691430 | 1.550003 | 0.087* | |
C19 | 0.46305 (10) | 0.63785 (9) | 1.4430 (3) | 0.0714 (7) | |
H19 | 0.443956 | 0.627485 | 1.520741 | 0.086* | |
C20 | 0.45852 (8) | 0.61441 (8) | 1.3144 (2) | 0.0556 (5) | |
H20 | 0.436309 | 0.588537 | 1.303791 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.092 (3) | 0.118 (3) | 0.093 (3) | −0.055 (2) | 0.009 (2) | −0.002 (2) |
C2A | 0.0903 (19) | 0.0684 (16) | 0.0790 (18) | −0.0305 (14) | −0.0128 (15) | 0.0055 (13) |
C3A | 0.0578 (14) | 0.0513 (14) | 0.0580 (15) | −0.0049 (11) | −0.0094 (12) | −0.0071 (12) |
C1B | 0.060 (4) | 0.060 (5) | 0.071 (5) | −0.001 (3) | 0.005 (3) | 0.003 (3) |
C2B | 0.081 (5) | 0.082 (5) | 0.084 (5) | −0.001 (2) | 0.000 (2) | −0.004 (2) |
C3B | 0.060 (4) | 0.061 (4) | 0.059 (4) | −0.001 (2) | −0.002 (2) | −0.002 (2) |
N1 | 0.0518 (10) | 0.0524 (10) | 0.0620 (12) | −0.0028 (8) | −0.0085 (9) | −0.0123 (9) |
C4 | 0.0460 (11) | 0.0499 (11) | 0.0508 (11) | 0.0097 (9) | −0.0066 (9) | −0.0037 (9) |
C5 | 0.0471 (11) | 0.0411 (10) | 0.0440 (10) | 0.0058 (8) | −0.0026 (9) | 0.0001 (8) |
C6 | 0.0674 (15) | 0.0805 (16) | 0.0539 (13) | 0.0079 (12) | −0.0086 (11) | −0.0185 (12) |
C7 | 0.0650 (13) | 0.0431 (11) | 0.0428 (10) | 0.0069 (9) | 0.0047 (10) | 0.0027 (9) |
O1 | 0.1109 (14) | 0.0413 (8) | 0.0649 (10) | 0.0050 (8) | 0.0316 (10) | 0.0050 (7) |
N2 | 0.0557 (10) | 0.0402 (9) | 0.0528 (10) | 0.0032 (7) | 0.0092 (8) | 0.0039 (8) |
C8 | 0.0553 (12) | 0.0474 (11) | 0.0432 (10) | −0.0078 (9) | 0.0026 (9) | −0.0018 (9) |
C9 | 0.0566 (13) | 0.0656 (14) | 0.0598 (13) | 0.0030 (11) | 0.0044 (11) | 0.0078 (11) |
C10 | 0.0574 (14) | 0.094 (2) | 0.0726 (16) | 0.0023 (13) | 0.0121 (13) | 0.0023 (15) |
C11 | 0.0698 (17) | 0.0887 (19) | 0.0671 (15) | −0.0283 (15) | 0.0151 (13) | −0.0060 (14) |
C12 | 0.100 (2) | 0.0582 (14) | 0.0691 (16) | −0.0249 (14) | 0.0257 (15) | −0.0036 (12) |
C13 | 0.0837 (17) | 0.0497 (12) | 0.0646 (14) | −0.0042 (11) | 0.0186 (13) | 0.0022 (11) |
C14 | 0.0398 (10) | 0.0369 (9) | 0.0459 (10) | 0.0048 (7) | −0.0006 (8) | 0.0017 (8) |
O2 | 0.0458 (7) | 0.0411 (7) | 0.0521 (8) | −0.0017 (6) | 0.0064 (6) | −0.0013 (6) |
N3 | 0.0581 (10) | 0.0397 (9) | 0.0462 (9) | −0.0063 (7) | 0.0079 (8) | −0.0011 (7) |
C15 | 0.0453 (10) | 0.0369 (10) | 0.0501 (11) | 0.0060 (8) | 0.0033 (9) | −0.0027 (8) |
C16 | 0.0558 (12) | 0.0415 (11) | 0.0645 (13) | −0.0025 (9) | 0.0075 (10) | −0.0076 (10) |
C17 | 0.0664 (15) | 0.0504 (12) | 0.0789 (16) | −0.0022 (11) | 0.0022 (13) | −0.0192 (12) |
C18 | 0.0843 (18) | 0.0642 (15) | 0.0694 (16) | 0.0026 (13) | 0.0052 (14) | −0.0263 (13) |
C19 | 0.0795 (17) | 0.0749 (16) | 0.0598 (14) | −0.0014 (13) | 0.0221 (13) | −0.0151 (13) |
C20 | 0.0565 (12) | 0.0522 (12) | 0.0580 (13) | −0.0043 (9) | 0.0133 (10) | −0.0099 (10) |
C1A—C2A | 1.442 (6) | C7—N2 | 1.369 (3) |
C1A—H1A | 0.9800 | N2—C8 | 1.414 (3) |
C1A—H1B | 0.9800 | N2—H2N | 0.88 (2) |
C1A—H1C | 0.9800 | C8—C9 | 1.382 (3) |
C2A—C3A | 1.506 (5) | C8—C13 | 1.389 (3) |
C2A—H2A | 0.9900 | C9—C10 | 1.390 (3) |
C2A—H2B | 0.9900 | C9—H9 | 0.9500 |
C3A—N1 | 1.457 (3) | C10—C11 | 1.376 (4) |
C3A—H3A | 0.9900 | C10—H10 | 0.9500 |
C3A—H3B | 0.9900 | C11—C12 | 1.368 (4) |
C1B—C2B | 1.435 (14) | C11—H11 | 0.9500 |
C1B—H1D | 0.9800 | C12—C13 | 1.384 (3) |
C1B—H1E | 0.9800 | C12—H12 | 0.9500 |
C1B—H1F | 0.9800 | C13—H13 | 0.9500 |
C2B—C3B | 1.477 (14) | C14—O2 | 1.257 (2) |
C2B—H2C | 0.9900 | C14—N3 | 1.366 (2) |
C2B—H2D | 0.9900 | N3—C15 | 1.410 (3) |
C3B—N1 | 1.580 (12) | N3—H3N | 0.90 (3) |
C3B—H3C | 0.9900 | C15—C20 | 1.387 (3) |
C3B—H3D | 0.9900 | C15—C16 | 1.395 (3) |
N1—C4 | 1.331 (3) | C16—C17 | 1.380 (3) |
N1—H1N | 0.91 (2) | C16—H16 | 0.9500 |
C4—C5 | 1.394 (3) | C17—C18 | 1.370 (4) |
C4—C6 | 1.508 (3) | C17—H17 | 0.9500 |
C5—C14 | 1.463 (3) | C18—C19 | 1.373 (4) |
C5—C7 | 1.485 (3) | C18—H18 | 0.9500 |
C6—H6A | 0.9800 | C19—C20 | 1.385 (3) |
C6—H6B | 0.9800 | C19—H19 | 0.9500 |
C6—H6C | 0.9800 | C20—H20 | 0.9500 |
C7—O1 | 1.234 (2) | ||
C2A—C1A—H1A | 109.5 | H6A—C6—H6C | 109.5 |
C2A—C1A—H1B | 109.5 | H6B—C6—H6C | 109.5 |
H1A—C1A—H1B | 109.5 | O1—C7—N2 | 121.7 (2) |
C2A—C1A—H1C | 109.5 | O1—C7—C5 | 123.24 (19) |
H1A—C1A—H1C | 109.5 | N2—C7—C5 | 114.91 (17) |
H1B—C1A—H1C | 109.5 | C7—N2—C8 | 127.97 (18) |
C1A—C2A—C3A | 115.7 (3) | C7—N2—H2N | 115.9 (14) |
C1A—C2A—H2A | 108.4 | C8—N2—H2N | 115.3 (14) |
C3A—C2A—H2A | 108.4 | C9—C8—C13 | 119.2 (2) |
C1A—C2A—H2B | 108.4 | C9—C8—N2 | 117.63 (18) |
C3A—C2A—H2B | 108.4 | C13—C8—N2 | 123.1 (2) |
H2A—C2A—H2B | 107.4 | C8—C9—C10 | 120.2 (2) |
N1—C3A—C2A | 108.1 (3) | C8—C9—H9 | 119.9 |
N1—C3A—H3A | 110.1 | C10—C9—H9 | 119.9 |
C2A—C3A—H3A | 110.1 | C11—C10—C9 | 120.4 (3) |
N1—C3A—H3B | 110.1 | C11—C10—H10 | 119.8 |
C2A—C3A—H3B | 110.1 | C9—C10—H10 | 119.8 |
H3A—C3A—H3B | 108.4 | C12—C11—C10 | 119.3 (2) |
C2B—C1B—H1D | 109.5 | C12—C11—H11 | 120.4 |
C2B—C1B—H1E | 109.5 | C10—C11—H11 | 120.4 |
H1D—C1B—H1E | 109.5 | C11—C12—C13 | 121.2 (2) |
C2B—C1B—H1F | 109.5 | C11—C12—H12 | 119.4 |
H1D—C1B—H1F | 109.5 | C13—C12—H12 | 119.4 |
H1E—C1B—H1F | 109.5 | C12—C13—C8 | 119.7 (2) |
C1B—C2B—C3B | 126.9 (13) | C12—C13—H13 | 120.1 |
C1B—C2B—H2C | 105.6 | C8—C13—H13 | 120.1 |
C3B—C2B—H2C | 105.6 | O2—C14—N3 | 120.55 (18) |
C1B—C2B—H2D | 105.6 | O2—C14—C5 | 123.10 (17) |
C3B—C2B—H2D | 105.6 | N3—C14—C5 | 116.35 (17) |
H2C—C2B—H2D | 106.1 | C14—N3—C15 | 129.51 (17) |
C2B—C3B—N1 | 113.2 (10) | C14—N3—H3N | 113.2 (16) |
C2B—C3B—H3C | 108.9 | C15—N3—H3N | 117.2 (16) |
N1—C3B—H3C | 108.9 | C20—C15—C16 | 118.78 (19) |
C2B—C3B—H3D | 108.9 | C20—C15—N3 | 125.00 (18) |
N1—C3B—H3D | 108.9 | C16—C15—N3 | 116.23 (18) |
H3C—C3B—H3D | 107.8 | C17—C16—C15 | 120.7 (2) |
C4—N1—C3A | 123.8 (2) | C17—C16—H16 | 119.7 |
C4—N1—C3B | 141.3 (6) | C15—C16—H16 | 119.7 |
C4—N1—H1N | 116.8 (15) | C18—C17—C16 | 120.4 (2) |
C3A—N1—H1N | 119.5 (15) | C18—C17—H17 | 119.8 |
C3B—N1—H1N | 100.4 (16) | C16—C17—H17 | 119.8 |
N1—C4—C5 | 121.78 (19) | C17—C18—C19 | 119.2 (2) |
N1—C4—C6 | 115.5 (2) | C17—C18—H18 | 120.4 |
C5—C4—C6 | 122.6 (2) | C19—C18—H18 | 120.4 |
C4—C5—C14 | 121.24 (18) | C18—C19—C20 | 121.6 (2) |
C4—C5—C7 | 120.47 (18) | C18—C19—H19 | 119.2 |
C14—C5—C7 | 118.27 (17) | C20—C19—H19 | 119.2 |
C4—C6—H6A | 109.5 | C19—C20—C15 | 119.3 (2) |
C4—C6—H6B | 109.5 | C19—C20—H20 | 120.3 |
H6A—C6—H6B | 109.5 | C15—C20—H20 | 120.3 |
C4—C6—H6C | 109.5 | ||
C1A—C2A—C3A—N1 | 65.0 (4) | C8—C9—C10—C11 | −0.4 (4) |
C1B—C2B—C3B—N1 | −46 (2) | C9—C10—C11—C12 | −1.0 (4) |
C2A—C3A—N1—C4 | 178.5 (3) | C10—C11—C12—C13 | 1.3 (4) |
C2B—C3B—N1—C4 | −116.6 (12) | C11—C12—C13—C8 | −0.2 (4) |
C3A—N1—C4—C5 | 174.5 (2) | C9—C8—C13—C12 | −1.3 (4) |
C3B—N1—C4—C5 | −166.6 (8) | N2—C8—C13—C12 | −179.3 (2) |
C3A—N1—C4—C6 | −1.1 (3) | C4—C5—C14—O2 | 9.5 (3) |
C3B—N1—C4—C6 | 17.9 (9) | C7—C5—C14—O2 | −168.94 (17) |
N1—C4—C5—C14 | −7.0 (3) | C4—C5—C14—N3 | −170.85 (17) |
C6—C4—C5—C14 | 168.25 (18) | C7—C5—C14—N3 | 10.7 (2) |
N1—C4—C5—C7 | 171.42 (18) | O2—C14—N3—C15 | 9.3 (3) |
C6—C4—C5—C7 | −13.4 (3) | C5—C14—N3—C15 | −170.35 (18) |
C4—C5—C7—O1 | 136.4 (2) | C14—N3—C15—C20 | −14.1 (3) |
C14—C5—C7—O1 | −45.1 (3) | C14—N3—C15—C16 | 166.21 (19) |
C4—C5—C7—N2 | −47.7 (3) | C20—C15—C16—C17 | −0.4 (3) |
C14—C5—C7—N2 | 130.73 (19) | N3—C15—C16—C17 | 179.2 (2) |
O1—C7—N2—C8 | −5.4 (3) | C15—C16—C17—C18 | 0.9 (4) |
C5—C7—N2—C8 | 178.67 (19) | C16—C17—C18—C19 | −0.5 (4) |
C7—N2—C8—C9 | 161.2 (2) | C17—C18—C19—C20 | −0.3 (4) |
C7—N2—C8—C13 | −20.8 (3) | C18—C19—C20—C15 | 0.7 (4) |
C13—C8—C9—C10 | 1.6 (3) | C16—C15—C20—C19 | −0.3 (3) |
N2—C8—C9—C10 | 179.6 (2) | N3—C15—C20—C19 | 180.0 (2) |
Cg2 is the centroid of the C15–C20 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2 | 0.91 (2) | 1.92 (2) | 2.638 (2) | 135 (2) |
N3—H3N···O1 | 0.90 (3) | 1.94 (3) | 2.712 (2) | 144 (2) |
C6—H6B···N2 | 0.98 | 2.46 | 2.968 (3) | 112 |
C13—H13···O1 | 0.95 | 2.33 | 2.879 (3) | 116 |
C20—H20···O2 | 0.95 | 2.30 | 2.887 (3) | 119 |
N2—H2N···O2i | 0.88 (2) | 2.08 (2) | 2.914 (2) | 157 (2) |
C9—H9···O2i | 0.95 | 2.91 | 3.622 (3) | 133 |
C13—H13···Cg2ii | 0.95 | 3.37 | 3.960 (3) | 122 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, y, z−1. |
Plane 1 | Plane 2 | (I) | (II) |
N1/C4/C5 | N3/C14/O2 | 10.1 (4) | 8.0 (3) |
N1/C4/C5 | N2/C7/O1 | 49.0 (2) | 51.5 (3) |
N2/C7/O1 | phenyl C8–C13 | 26.8 (2) | 23.6 (2) |
N3/C14/O2 | phenyl C15–C20 | 17.1 (3) | 10.4 (2) |
Acknowledgements
The authors thank Anke Schwarzer for help with the discussion of intermolecular interactions and the TU Bergakademie Freiberg (Freiberg, Germany) for financial support.
Funding information
Funding for this research was provided by: Open Access Funding by the Publication Fund of the TU Bergakademie Freiberg.
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