In the solid state, the title compound, adopts the keto–amine tautomeric form, with the H atom attached to the N atom, which participates in an intramolecular N—H⋯O hydrogen bond with an S(6) ring motif. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds to generate C(16) chains propagating in the [301] direction.
Keywords: crystal structure, Schiff bases, pyrazolone derivatives, keto–amine tautomeric form, hydrogen bonding, π–π stacking interactions
Abstract
In the solid state, the title compound, C20H19N3O2, adopts the keto–amine tautomeric form, with the H atom attached to the N atom, which participates in an intramolecular N—H⋯O hydrogen bond with an S(6) ring motif. The dihedral angles between the pyrazole ring and the phenyl and benzene rings are 3.69 (10) and 46.47 (9)°, respectively. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, generating C(16) chains propagating in [301]. Weak aromatic π–π stacking interactions [centroid–centroid distances = 3.6123 (10) and 3.6665 (10) Å] link the chains into a three-dimensional network.
Chemical context
The chemistry of pyrazolone derivatives has attracted much attention because of their interesting structural properties and applications in diverse areas. Pyrazolone derivatives are also used as starting materials for the synthesis of biologically active compounds. Ethylidene species are of interest for this reaction system because they are a secondary C2 reaction intermediate, after ethyl species, expected from ethane by cleavage of two C—H bonds at the same carbon atom (Brooks et al., 2011 ▸).
Schiff base compounds have received considerable attention for many years, primarily due to their importance in the development of coordination chemistry related to magnetism (Weber et al., 2007 ▸), catalysis (Chen et al., 2008 ▸) and biological processes (May et al., 2004 ▸). In general, O-hydroxy Schiff bases exhibit two possible tautomeric forms, the enol–imine and keto–amine forms. Depending on the tautomers, two types of intramolecular hydrogen bonds are possible: O—H⋯N in the enol–imine and N—H⋯O in the keto–amine form. Schiff bases derived from acyl pyrazones and aromatic amines have been prepared as antimicrobial agents (Parmar et al., 2015 ▸) and also as ligands for the formation of metal-ion complexes (Jayarajan et al., 2010 ▸; Moorjani et al., 2010 ▸). A compound similar to the title compound, 5-methyl-2-phenyl-4-{1-[(pyridin-2-ylmethyl)-amino]-ethylidene}-2,4-dihydro-pyrazol-3-one derived from acyl pyrazolone and aliphatic amine was reported to possesses the amino-one structure (Amarasekara et al., 2009 ▸).
Structural commentary
In the title compound (Fig. 1 ▸) the bond lengths indicate double-bond character for the C7=O1 [1.2472 (19) Å [and C8=C11 [1.389 (2) Å] bonds and single-bond character for the C11—N3 [1.339 (2) Å] and N3—C13 [1.413 (2) Å] bonds. Furthermore, the H1 atom was found to be located on atom N3, confirming that the title compound exists in the keto–amine form in the solid state.
Figure 1.
An ORTEP view of title compound, showing 30% probability displacement ellipsoids. The dashed line shows the intramolecular N—H⋯O hydrogen bond.
An intramolecular N3—H3A⋯O1 hydrogen bond is observed (Table 1 ▸, Fig. 1 ▸). This interaction generates an S(6) ring motif. The 4-acetylphenylamino ethylidene and phenyl pyrazol groups of the molecule are nearly planar, with r.m.s. deviations from the mean plane of 0.0430 and 0.0256 Å, respectively. The dihedral angle between these two groups is 47.81 (3)°. The dihedral angles between the pyrazole ring and the phenyl and benzene rings are 3.69 (10) and 46.47 (9)°, respectively. Similar results were observed in N-[(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene)(phenyl)methyl]glycine ethyl ester (Zhang et al., 2004 ▸), ethyl 2-{[(1Z)-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene)(p-tolyl)methyl]amino}-3-phenylpropanoate (Zhang et al., 2010 ▸) and 4-{[3,4-dihydro-5-methyl-3-oxo-2-phenyl-2H-pyrazol-4-ylidene](phenyl)methylamino}-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (Wang et al., 2003 ▸).
Table 1. Hydrogen-bond geometry (, ).
| DHA | DH | HA | D A | DHA |
|---|---|---|---|---|
| N3H3AO1 | 0.90(2) | 1.88(2) | 2.6527(18) | 144(2) |
| C4H4O2i | 0.93 | 2.57 | 3.403(2) | 150 |
Symmetry code: (i) 
.
Supramolecular features
In the crystal, the molecules are linked by C4—H4⋯O2 hydrogen bonds (Fig. 2 ▸, Table 1 ▸). The chains formed by these bonds along the c-axis direction are connected by two weak π–π stacking interactions [Cg1⋯Cg1(1 − x, 1 − y, 1 − z) = 3.6123 (10) and Cg1⋯Cg2(
+ x, 
− y, + z) = 3.6665 (10) Å; Cg1 and Cg2 are the centroids of the C7–C9/N1,N2 and C13–C18 rings, respectively], forming a three-dimensional network (Fig. 3 ▸).
Figure 2.
A packing diagram for title compound, showing the intermolecular C—H⋯O and intramolecular N—H⋯O hydrogen bonds. [Symmetry code: (i) + x, − y, + z.]
Figure 3.
A packing diagram for title compound showing the π–π stacking interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity. Cg1 and Cg2 are the centroids of the pyrozolone and C13–C18 rings, respectively. [Symmetry codes: (ii) 1 − x, 1 − y, 1 − z; (iii) + x, − y, + z.]
Synthesis and crystallization
The title compound was obtained by refluxing equimolar quantities of 4-acetyl-3-methyl-1-phenyl-2-pyrazolin-5-one and 4-aminoacetophenone (10 mmol) in ethanol for 2 h. On cooling, the yellow precipitate was collected by filtration and recrystallized from an ethanol–dioxan solvent mixture as yellow slabs. Yield (73%); m.p. 439–441; IR (KBr) ν = 3450, 3350, 3300 (NH2, NH), 1676,1628 (C=O, s) cm−1; MS, m/z = 333.8. Calculated for C20H19N3O2: C, 72.05; H, 5.74; N, 12.60. Found: C, 72.20; H, 5.62; N, 12.78%.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The H atom bonded to the N atom was located in a difference Fourier map and was refined freely. All other H atoms were refined using a riding model with d(C—H) = 0.93 Å (U iso=1.2U eq of the parent atom) for aromatic C atoms and d(C—H) = 0.96 Å (U iso=1.5U eq of the parent atom) for methyl C atoms.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C20H19N3O2 |
| M r | 333.38 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 296 |
| a, b, c () | 11.8549(4), 11.6070(5), 13.1591(5) |
| () | 107.425(3) |
| V (3) | 1727.60(12) |
| Z | 4 |
| Radiation type | Mo K |
| (mm1) | 0.09 |
| Crystal size (mm) | 0.80 0.57 0.10 |
| Data collection | |
| Diffractometer | Stoe IPDS 2 |
| Absorption correction | Integration (X-RED32; Stoe Cie, 2002 ▸) |
| T min, T max | 0.935, 0.991 |
| No. of measured, independent and observed [I > 2(I)] reflections | 25592, 3584, 2772 |
| R int | 0.056 |
| (sin /)max (1) | 0.628 |
| Refinement | |
| R[F 2 > 2(F 2)], wR(F 2), S | 0.050, 0.126, 1.07 |
| No. of reflections | 3584 |
| No. of parameters | 231 |
| No. of restraints | 1 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| max, min (e 3) | 0.17, 0.16 |
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989014026899/hb7330sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014026899/hb7330Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989014026899/hb7330Isup3.cml
CCDC reference: 1038012
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).
supplementary crystallographic information
Crystal data
| C20H19N3O2 | F(000) = 704 |
| Mr = 333.38 | Dx = 1.282 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| a = 11.8549 (4) Å | Cell parameters from 3705 reflections |
| b = 11.6070 (5) Å | θ = 2.4–26.7° |
| c = 13.1591 (5) Å | µ = 0.09 mm−1 |
| β = 107.425 (3)° | T = 296 K |
| V = 1727.60 (12) Å3 | Slab, yellow |
| Z = 4 | 0.80 × 0.57 × 0.10 mm |
Data collection
| Stoe IPDS 2 diffractometer | 2772 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.056 |
| ω–scan rotation method | θmax = 26.5°, θmin = 2.4° |
| Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | h = −14→14 |
| Tmin = 0.935, Tmax = 0.991 | k = −14→14 |
| 25592 measured reflections | l = −16→16 |
| 3584 independent reflections |
Refinement
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: mixed |
| wR(F2) = 0.126 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.07 | w = 1/[σ2(Fo2) + (0.0592P)2 + 0.1897P] where P = (Fo2 + 2Fc2)/3 |
| 3584 reflections | (Δ/σ)max < 0.001 |
| 231 parameters | Δρmax = 0.17 e Å−3 |
| 1 restraint | Δρmin = −0.16 e Å−3 |
Special details
| Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.68663 (14) | 0.70961 (15) | 0.55951 (13) | 0.0594 (4) | |
| C2 | 0.78901 (16) | 0.70082 (19) | 0.64551 (16) | 0.0771 (5) | |
| H2 | 0.7865 | 0.6647 | 0.7079 | 0.093* | |
| C3 | 0.89330 (18) | 0.7453 (2) | 0.6381 (2) | 0.0931 (7) | |
| H3 | 0.9614 | 0.7388 | 0.6957 | 0.112* | |
| C4 | 0.89876 (19) | 0.7993 (2) | 0.5472 (2) | 0.0923 (7) | |
| H4 | 0.9701 | 0.8287 | 0.5427 | 0.111* | |
| C5 | 0.79784 (19) | 0.8096 (2) | 0.46270 (19) | 0.0838 (6) | |
| H5 | 0.8011 | 0.8472 | 0.4012 | 0.101* | |
| C6 | 0.69112 (16) | 0.76487 (17) | 0.46756 (16) | 0.0698 (5) | |
| H6 | 0.6234 | 0.7719 | 0.4097 | 0.084* | |
| C7 | 0.47116 (14) | 0.65691 (14) | 0.49191 (12) | 0.0542 (4) | |
| C8 | 0.39461 (14) | 0.60235 (13) | 0.54463 (12) | 0.0530 (4) | |
| C9 | 0.46974 (15) | 0.57875 (15) | 0.65068 (12) | 0.0583 (4) | |
| C10 | 0.4410 (2) | 0.5216 (2) | 0.74124 (14) | 0.0825 (6) | |
| H10A | 0.4126 | 0.4450 | 0.7208 | 0.099* | |
| H10B | 0.3811 | 0.5651 | 0.7598 | 0.099* | |
| H10C | 0.5107 | 0.5179 | 0.8015 | 0.099* | |
| C11 | 0.27542 (14) | 0.58305 (14) | 0.49366 (12) | 0.0536 (4) | |
| C12 | 0.19337 (16) | 0.53059 (17) | 0.54741 (14) | 0.0685 (5) | |
| H12A | 0.1621 | 0.5898 | 0.5822 | 0.103* | |
| H12B | 0.2356 | 0.4753 | 0.5992 | 0.103* | |
| H12C | 0.1296 | 0.4929 | 0.4954 | 0.103* | |
| C13 | 0.11905 (14) | 0.61084 (14) | 0.31950 (12) | 0.0545 (4) | |
| C14 | 0.10632 (15) | 0.57899 (16) | 0.21567 (13) | 0.0633 (4) | |
| H14 | 0.1718 | 0.5538 | 0.1968 | 0.076* | |
| C15 | −0.00252 (15) | 0.58422 (17) | 0.13969 (14) | 0.0661 (5) | |
| H15 | −0.0096 | 0.5630 | 0.0699 | 0.079* | |
| C16 | −0.10156 (14) | 0.62055 (15) | 0.16568 (13) | 0.0595 (4) | |
| C17 | −0.08768 (15) | 0.65196 (16) | 0.27021 (15) | 0.0663 (5) | |
| H17 | −0.1534 | 0.6762 | 0.2892 | 0.080* | |
| C18 | 0.02076 (15) | 0.64829 (16) | 0.34677 (14) | 0.0647 (4) | |
| H18 | 0.0281 | 0.6708 | 0.4163 | 0.078* | |
| C19 | −0.22040 (16) | 0.63304 (18) | 0.08467 (17) | 0.0739 (5) | |
| C20 | −0.23519 (19) | 0.5992 (2) | −0.02808 (16) | 0.0863 (6) | |
| H20A | −0.2151 | 0.5193 | −0.0307 | 0.104* | |
| H20B | −0.1841 | 0.6453 | −0.0560 | 0.104* | |
| H20C | −0.3158 | 0.6111 | −0.0700 | 0.104* | |
| N1 | 0.57996 (12) | 0.66251 (12) | 0.56781 (10) | 0.0576 (3) | |
| N2 | 0.57755 (13) | 0.61356 (13) | 0.66442 (11) | 0.0639 (4) | |
| N3 | 0.23507 (12) | 0.61234 (13) | 0.39067 (11) | 0.0586 (4) | |
| O1 | 0.44674 (10) | 0.69356 (12) | 0.39873 (9) | 0.0673 (3) | |
| O2 | −0.30253 (13) | 0.67134 (17) | 0.11080 (14) | 0.1087 (6) | |
| H3A | 0.2925 (16) | 0.6339 (18) | 0.3635 (15) | 0.086 (6)* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0516 (9) | 0.0619 (10) | 0.0649 (10) | −0.0006 (7) | 0.0176 (7) | −0.0177 (8) |
| C2 | 0.0589 (10) | 0.0909 (14) | 0.0741 (12) | −0.0009 (10) | 0.0089 (9) | −0.0204 (10) |
| C3 | 0.0577 (11) | 0.1136 (18) | 0.1009 (17) | −0.0079 (11) | 0.0128 (11) | −0.0380 (15) |
| C4 | 0.0619 (12) | 0.1057 (17) | 0.1176 (18) | −0.0214 (11) | 0.0397 (12) | −0.0490 (15) |
| C5 | 0.0779 (13) | 0.0907 (15) | 0.0948 (15) | −0.0168 (11) | 0.0439 (12) | −0.0234 (12) |
| C6 | 0.0608 (10) | 0.0796 (12) | 0.0721 (11) | −0.0067 (9) | 0.0247 (9) | −0.0135 (9) |
| C7 | 0.0521 (8) | 0.0580 (9) | 0.0512 (8) | 0.0024 (7) | 0.0136 (7) | −0.0054 (7) |
| C8 | 0.0568 (9) | 0.0529 (9) | 0.0501 (8) | 0.0012 (7) | 0.0170 (7) | −0.0024 (7) |
| C9 | 0.0649 (10) | 0.0575 (9) | 0.0504 (8) | 0.0038 (8) | 0.0140 (7) | −0.0007 (7) |
| C10 | 0.0912 (14) | 0.0940 (15) | 0.0590 (10) | −0.0028 (12) | 0.0177 (10) | 0.0137 (10) |
| C11 | 0.0579 (9) | 0.0505 (9) | 0.0537 (8) | 0.0007 (7) | 0.0186 (7) | −0.0032 (7) |
| C12 | 0.0693 (11) | 0.0700 (11) | 0.0697 (11) | −0.0055 (9) | 0.0263 (9) | 0.0063 (9) |
| C13 | 0.0499 (8) | 0.0561 (9) | 0.0568 (9) | −0.0027 (7) | 0.0148 (7) | 0.0001 (7) |
| C14 | 0.0529 (9) | 0.0800 (12) | 0.0587 (9) | 0.0079 (8) | 0.0195 (7) | −0.0031 (8) |
| C15 | 0.0619 (10) | 0.0783 (12) | 0.0554 (9) | 0.0041 (9) | 0.0133 (8) | −0.0057 (8) |
| C16 | 0.0504 (9) | 0.0597 (10) | 0.0663 (10) | −0.0039 (7) | 0.0145 (7) | 0.0045 (8) |
| C17 | 0.0525 (9) | 0.0752 (12) | 0.0760 (11) | 0.0051 (8) | 0.0267 (8) | 0.0036 (9) |
| C18 | 0.0620 (10) | 0.0753 (12) | 0.0602 (9) | 0.0041 (9) | 0.0233 (8) | −0.0053 (8) |
| C19 | 0.0530 (10) | 0.0735 (12) | 0.0898 (13) | −0.0073 (9) | 0.0133 (9) | 0.0103 (10) |
| C20 | 0.0737 (13) | 0.0826 (14) | 0.0827 (13) | −0.0088 (11) | −0.0069 (10) | 0.0038 (11) |
| N1 | 0.0527 (7) | 0.0649 (8) | 0.0527 (7) | 0.0008 (6) | 0.0120 (6) | −0.0036 (6) |
| N2 | 0.0657 (9) | 0.0692 (9) | 0.0519 (7) | 0.0039 (7) | 0.0104 (6) | 0.0015 (6) |
| N3 | 0.0496 (7) | 0.0718 (9) | 0.0546 (8) | −0.0041 (6) | 0.0158 (6) | −0.0003 (6) |
| O1 | 0.0583 (7) | 0.0915 (9) | 0.0505 (6) | −0.0052 (6) | 0.0139 (5) | 0.0071 (6) |
| O2 | 0.0523 (8) | 0.1516 (16) | 0.1176 (13) | 0.0109 (9) | 0.0185 (8) | 0.0077 (11) |
Geometric parameters (Å, º)
| C1—C6 | 1.385 (3) | C11—C12 | 1.493 (2) |
| C1—C2 | 1.393 (2) | C12—H12A | 0.9600 |
| C1—N1 | 1.412 (2) | C12—H12B | 0.9600 |
| C2—C3 | 1.370 (3) | C12—H12C | 0.9600 |
| C2—H2 | 0.9300 | C13—C14 | 1.380 (2) |
| C3—C4 | 1.370 (4) | C13—C18 | 1.388 (2) |
| C3—H3 | 0.9300 | C13—N3 | 1.413 (2) |
| C4—C5 | 1.373 (3) | C14—C15 | 1.377 (2) |
| C4—H4 | 0.9300 | C14—H14 | 0.9300 |
| C5—C6 | 1.387 (3) | C15—C16 | 1.383 (2) |
| C5—H5 | 0.9300 | C15—H15 | 0.9300 |
| C6—H6 | 0.9300 | C16—C17 | 1.384 (2) |
| C7—O1 | 1.2472 (19) | C16—C19 | 1.498 (2) |
| C7—N1 | 1.376 (2) | C17—C18 | 1.376 (2) |
| C7—C8 | 1.443 (2) | C17—H17 | 0.9300 |
| C8—C11 | 1.389 (2) | C18—H18 | 0.9300 |
| C8—C9 | 1.439 (2) | C19—O2 | 1.210 (2) |
| C9—N2 | 1.300 (2) | C19—C20 | 1.494 (3) |
| C9—C10 | 1.490 (2) | C20—H20A | 0.9600 |
| C10—H10A | 0.9600 | C20—H20B | 0.9600 |
| C10—H10B | 0.9600 | C20—H20C | 0.9600 |
| C10—H10C | 0.9600 | N1—N2 | 1.4006 (19) |
| C11—N3 | 1.339 (2) | N3—H3A | 0.895 (15) |
| C6—C1—C2 | 119.44 (17) | H12A—C12—H12B | 109.5 |
| C6—C1—N1 | 121.12 (15) | C11—C12—H12C | 109.5 |
| C2—C1—N1 | 119.44 (17) | H12A—C12—H12C | 109.5 |
| C3—C2—C1 | 120.0 (2) | H12B—C12—H12C | 109.5 |
| C3—C2—H2 | 120.0 | C14—C13—C18 | 119.26 (15) |
| C1—C2—H2 | 120.0 | C14—C13—N3 | 117.11 (14) |
| C4—C3—C2 | 120.9 (2) | C18—C13—N3 | 123.42 (15) |
| C4—C3—H3 | 119.5 | C15—C14—C13 | 120.55 (15) |
| C2—C3—H3 | 119.5 | C15—C14—H14 | 119.7 |
| C3—C4—C5 | 119.3 (2) | C13—C14—H14 | 119.7 |
| C3—C4—H4 | 120.3 | C14—C15—C16 | 120.94 (16) |
| C5—C4—H4 | 120.3 | C14—C15—H15 | 119.5 |
| C4—C5—C6 | 121.1 (2) | C16—C15—H15 | 119.5 |
| C4—C5—H5 | 119.5 | C15—C16—C17 | 117.95 (15) |
| C6—C5—H5 | 119.5 | C15—C16—C19 | 122.73 (16) |
| C1—C6—C5 | 119.22 (19) | C17—C16—C19 | 119.24 (16) |
| C1—C6—H6 | 120.4 | C18—C17—C16 | 121.75 (16) |
| C5—C6—H6 | 120.4 | C18—C17—H17 | 119.1 |
| O1—C7—N1 | 126.05 (15) | C16—C17—H17 | 119.1 |
| O1—C7—C8 | 128.90 (14) | C17—C18—C13 | 119.55 (16) |
| N1—C7—C8 | 105.04 (13) | C17—C18—H18 | 120.2 |
| C11—C8—C9 | 133.02 (15) | C13—C18—H18 | 120.2 |
| C11—C8—C7 | 122.26 (14) | O2—C19—C20 | 120.93 (18) |
| C9—C8—C7 | 104.71 (14) | O2—C19—C16 | 119.9 (2) |
| N2—C9—C8 | 111.89 (15) | C20—C19—C16 | 119.16 (18) |
| N2—C9—C10 | 118.56 (15) | C19—C20—H20A | 109.5 |
| C8—C9—C10 | 129.55 (16) | C19—C20—H20B | 109.5 |
| C9—C10—H10A | 109.5 | H20A—C20—H20B | 109.5 |
| C9—C10—H10B | 109.5 | C19—C20—H20C | 109.5 |
| H10A—C10—H10B | 109.5 | H20A—C20—H20C | 109.5 |
| C9—C10—H10C | 109.5 | H20B—C20—H20C | 109.5 |
| H10A—C10—H10C | 109.5 | C7—N1—N2 | 111.72 (13) |
| H10B—C10—H10C | 109.5 | C7—N1—C1 | 128.96 (14) |
| N3—C11—C8 | 116.82 (14) | N2—N1—C1 | 119.31 (13) |
| N3—C11—C12 | 119.81 (15) | C9—N2—N1 | 106.63 (13) |
| C8—C11—C12 | 123.36 (14) | C11—N3—C13 | 130.49 (14) |
| C11—C12—H12A | 109.5 | C11—N3—H3A | 113.1 (13) |
| C11—C12—H12B | 109.5 | C13—N3—H3A | 116.4 (13) |
| C6—C1—C2—C3 | −0.8 (3) | C15—C16—C17—C18 | 0.4 (3) |
| N1—C1—C2—C3 | 179.45 (18) | C19—C16—C17—C18 | −176.39 (17) |
| C1—C2—C3—C4 | 0.3 (3) | C16—C17—C18—C13 | −0.8 (3) |
| C2—C3—C4—C5 | 0.5 (3) | C14—C13—C18—C17 | 0.6 (3) |
| C3—C4—C5—C6 | −0.9 (3) | N3—C13—C18—C17 | 175.11 (17) |
| C2—C1—C6—C5 | 0.5 (3) | C15—C16—C19—O2 | −175.8 (2) |
| N1—C1—C6—C5 | −179.81 (16) | C17—C16—C19—O2 | 0.7 (3) |
| C4—C5—C6—C1 | 0.4 (3) | C15—C16—C19—C20 | 3.4 (3) |
| O1—C7—C8—C11 | −0.1 (3) | C17—C16—C19—C20 | 179.97 (18) |
| N1—C7—C8—C11 | 178.89 (14) | O1—C7—N1—N2 | 179.96 (15) |
| O1—C7—C8—C9 | −179.84 (17) | C8—C7—N1—N2 | 0.89 (17) |
| N1—C7—C8—C9 | −0.80 (16) | O1—C7—N1—C1 | 0.2 (3) |
| C11—C8—C9—N2 | −179.15 (17) | C8—C7—N1—C1 | −178.83 (15) |
| C7—C8—C9—N2 | 0.49 (19) | C6—C1—N1—C7 | 3.6 (3) |
| C11—C8—C9—C10 | 1.4 (3) | C2—C1—N1—C7 | −176.73 (16) |
| C7—C8—C9—C10 | −178.95 (18) | C6—C1—N1—N2 | −176.12 (16) |
| C9—C8—C11—N3 | −177.17 (17) | C2—C1—N1—N2 | 3.6 (2) |
| C7—C8—C11—N3 | 3.2 (2) | C8—C9—N2—N1 | 0.04 (19) |
| C9—C8—C11—C12 | 1.8 (3) | C10—C9—N2—N1 | 179.55 (16) |
| C7—C8—C11—C12 | −177.78 (16) | C7—N1—N2—C9 | −0.60 (19) |
| C18—C13—C14—C15 | 0.0 (3) | C1—N1—N2—C9 | 179.15 (14) |
| N3—C13—C14—C15 | −174.80 (16) | C8—C11—N3—C13 | −175.30 (16) |
| C13—C14—C15—C16 | −0.5 (3) | C12—C11—N3—C13 | 5.7 (3) |
| C14—C15—C16—C17 | 0.3 (3) | C14—C13—N3—C11 | −142.71 (18) |
| C14—C15—C16—C19 | 176.95 (17) | C18—C13—N3—C11 | 42.7 (3) |
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N3—H3A···O1 | 0.90 (2) | 1.88 (2) | 2.6527 (18) | 144 (2) |
| C4—H4···O2i | 0.93 | 2.57 | 3.403 (2) | 150 |
Symmetry code: (i) x+3/2, −y+3/2, z+1/2.
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989014026899/hb7330sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014026899/hb7330Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989014026899/hb7330Isup3.cml
CCDC reference: 1038012
Additional supporting information: crystallographic information; 3D view; checkCIF report