The title compound has an almost planar 1,2-dibenzylidenehydrazine backbone with an approximately orthogonal planar phenyl ethanone substituent on one of the imine C atoms. In the crystal, molecules are linked via C—H⋯O hydrogen bonds and C—H⋯π interactions, forming a three-dimensional structure.
Keywords: crystal structure, Schiff base, azines, dimers, C—H⋯π contacts
Abstract
The title compound, C21H16N2O, has an almost planar (r.m.s. deviation = 0.0074 Å) 1,2-dibenzylidenehydrazine backbone with an approximately orthogonal almost planar (r.m.s. deviation = 0.0368 Å) phenylethanone substituent on one of the imine C atoms. The dihedral angle between the two mean planes is 76.99 (4)°. In the crystal, molecules are linked via C—H⋯O hydrogen bonds and C—H⋯π contacts, forming a three-dimensional structure with molecules stacked along the a-axis direction.
Chemical context
Aromatic carbonyl compounds react easily with hydrazines to form hydrazones, which can condense with a second molecule of a carbonyl compound to yield an azine. As a result of their fascinating physical and chemical properties, azines and their derivatives have been utilized extensively in areas such as dyes (Kim et al., 2010 ▸) and non-linear fluorophores (Facchetti et al., 2002 ▸). They are also noted for their biological and pharmaceutical applications (Wadher et al., 2009 ▸; Pandeya et al., 1999 ▸). Furthermore, there are many reports of polyazines as highly conjugated polymers functioning in electronic, optoelectronic and photonic applications (Dudis et al., 1993 ▸). As part of our studies of Schiff base azines, the title compound was synthesized and its molecular and crystal structure are reported on herein.
Structural commentary
The molecule of the title compound, Fig. 1 ▸, comprises a 1,2-dibenzylidenehydrazine backbone with a phenyl ethanone substituent on atom C2. Both the hydrazine and ethanone fragments are approximately planar with r.m.s. deviations of 0.0074 Å from the O1/C1/C11–C16 mean plane and 0.0368 Å from the plane through the 16 atoms of the dibenzylidenehydrazine unit. The two mean planes are almost orthogonal with a dihedral angle of 76.99 (4)°. The molecule adopts a Z conformation with respect to the C2=N1 bond and an E conformation with respect to the C3=N2 bond, with the carbonyl atom O1 and the C11–C16 phenyl ring located on opposite sides of the dibenzylidenehydrazine plane. The bond lengths and angles in the title molecule agree reasonably well with those found in closely related structures (Abbasi et al., 2007 ▸; Wieland et al., 2011 ▸).
Figure 1.
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
Supramolecular features
In the crystal, a pair of C35—H35⋯O1 hydrogen bonds link adjacent molecules into dimers with 
(20) ring motifs (Fig. 2 ▸ and Table 1 ▸). Atom O1 is also involved in two further C—H⋯O hydrogen bonds, C3—H3⋯O1 and C32—H32⋯O1 that generate 
(6) ring motifs. These contacts link the dimers into stacks parallel to (011); see Table 1 ▸ and Fig. 2 ▸. Interestingly, neither of the hydrazine N atoms are involved in significantly close intermolecular contacts with the shortest intermolecular H12⋯N1 contact being ca 2.85 Å. A contribution to the packing is, however, made by a C—H⋯π interaction (Table 1 ▸). These interactions link molecules in a head-to-tail fashion, forming chains along c, as shown in Fig. 3 ▸. With 16 molecules in the orthorhombic unit cell, these various contacts combine to form a three dimensional structure with molecules stacked along the a-axis direction, as shown in Fig. 4 ▸.
Figure 2.
A view of the dimers formed via C—H⋯O contacts (blue dashed lines; see Table 1 ▸ for details) and linked into stacks running parallel to (011) in the crystal of the title compound.
Table 1. Hydrogen-bond geometry (, ).
Cg is the centroid of the C31C36 phenyl ring.
| DHA | DH | HA | D A | DHA |
|---|---|---|---|---|
| C35H35O1i | 0.95 | 2.61 | 3.337(3) | 134 |
| C3H3O1ii | 0.95 | 2.41 | 3.272(3) | 151 |
| C32H32O1ii | 0.95 | 2.68 | 3.478(3) | 141 |
| C26H26Cg iii | 0.95 | 2.97 | 3.699(3) | 135 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
.
Figure 3.
A view of the chains along the c-axis direction formed by C—H⋯π contacts in the crystal of the title compound (shown as green dotted lines with the ring centroids displayed as coloured spheres, see Table 1 ▸ for details).
Figure 4.
A view along the a-axis direction of the crystal packing of the title compound. Hydrogen bonds are drawn as blue dashed lines with a representative C—H⋯π contact shown as a green dotted line (see Table 1 ▸ for details).
Database survey
A search for the (benzylidenehydrazono)-1,2-diphenylethanone skeleton in the Cambridge Structural Database (Version 5.35, November 2013 with three updates; Groom & Allen, 2014 ▸) revealed only 7 similar compounds. The closest to the title structure are 2-{(Z)-2-[(E)-1-(2-hydroxyphenyl)methylidene]hydrazono}-1,2-diphenylethan-1-one (Abbasi et al., 2007 ▸), with an hydroxy substituent in the p position on the equivalent of the benzene ring, and 1,2-diphenyl-2-[4-(4-pyridyl)benzylidenehydrazono]ethan-1-one, with a pyridyl ring in the same position (Patra & Ng, 2009 ▸). Two reports of polymorphs of the symmetrical 2,2′-(1,2-hydrazinediylidene)-bis(diphenylethanone) have also appeared (Patra et al., 2009 ▸; Wieland et al., 2011 ▸)
Synthesis and crystallization
A mixture of benzaldehyde (0.01 mol, 1.06 g), benzil (0.01 mol, 2.10 g) and hydrazine hydrate (0.01 mol, 0.32 g) in 50 ml of ethanol containing 2 drops of acetic acid was refluxed for about 2 h. The reaction was monitored by TLC until completion. Excess solvent was evaporated under vacuum and the resulting yellow solid product was recrystallized from absolute ethanol to afford yellow needles of the title compound (m.p. 453 K, 75% yield). Analysis calculated for C21H16N2O (312.36): C 80.75, H 5.16, N 8.97%; found: C 80.73, H 5.17, N 9.01%.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The C-bound H atoms were included in calculated positions and treated as riding atoms: C—H = 0.95 Å with U iso = 1.2U eq(C).
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C21H16N2O |
| M r | 312.36 |
| Crystal system, space group | Orthorhombic, F2d d |
| Temperature (K) | 150 |
| a, b, c () | 8.1653(3), 27.6113(11), 29.6818(13) |
| V (3) | 6691.9(5) |
| Z | 16 |
| Radiation type | Mo K |
| (mm1) | 0.08 |
| Crystal size (mm) | 0.55 0.29 0.24 |
| Data collection | |
| Diffractometer | Bruker APEXII |
| Absorption correction | Multi-scan (SADABS; Bruker, 2006 ▸) |
| T min, T max | 0.884, 0.982 |
| No. of measured, independent and observed [I > 2(I)] reflections | 8049, 3350, 3036 |
| R int | 0.032 |
| (sin /)max (1) | 0.649 |
| Refinement | |
| R[F 2 > 2(F 2)], wR(F 2), S | 0.039, 0.094, 1.06 |
| No. of reflections | 3350 |
| No. of parameters | 217 |
| No. of restraints | 1 |
| H-atom treatment | H-atom parameters constrained |
| max, min (e 3) | 0.18, 0.16 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989014026358/su5029sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014026358/su5029Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989014026358/su5029Isup3.cml
CCDC reference: 1036846
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors acknowledge the Algerian Ministry of Higher Education and Scientific Research, the Algerian Directorate General for Scientific Research and Technological Development, and Ferhat Abbas Sétif 1 University for financial support. The Chemistry Department of the University of Otago is also thanked for support of the work of JS. Dr Lahcène Ouahab from the University of Rennes 1, France, is thanked for the data collection.
supplementary crystallographic information
Crystal data
| C21H16N2O | F(000) = 2624 |
| Mr = 312.36 | Dx = 1.240 Mg m−3 |
| Orthorhombic, F2dd | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: F -2d 2 | Cell parameters from 2807 reflections |
| a = 8.1653 (3) Å | θ = 2.7–27.3° |
| b = 27.6113 (11) Å | µ = 0.08 mm−1 |
| c = 29.6818 (13) Å | T = 150 K |
| V = 6691.9 (5) Å3 | Prism, yellow |
| Z = 16 | 0.55 × 0.29 × 0.24 mm |
Data collection
| Bruker APEXII diffractometer | 3036 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.032 |
| CCD rotation images, thin slices scans | θmax = 27.5°, θmin = 3.0° |
| Absorption correction: multi-scan (SADABS; Bruker, 2006) | h = −9→10 |
| Tmin = 0.884, Tmax = 0.982 | k = −35→24 |
| 8049 measured reflections | l = −38→38 |
| 3350 independent reflections |
Refinement
| Refinement on F2 | 1 restraint |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0407P)2 + 4.1058P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.06 | (Δ/σ)max < 0.001 |
| 3350 reflections | Δρmax = 0.18 e Å−3 |
| 217 parameters | Δρmin = −0.16 e Å−3 |
Special details
| Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C11 | 0.4692 (3) | 0.24563 (8) | 0.36467 (7) | 0.0255 (5) | |
| C12 | 0.4156 (3) | 0.28709 (9) | 0.34210 (7) | 0.0316 (5) | |
| H12 | 0.4758 | 0.3164 | 0.3444 | 0.038* | |
| C13 | 0.2746 (3) | 0.28525 (11) | 0.31643 (9) | 0.0426 (7) | |
| H13 | 0.2381 | 0.3134 | 0.3010 | 0.051* | |
| C14 | 0.1865 (3) | 0.24267 (12) | 0.31313 (10) | 0.0504 (8) | |
| H14 | 0.0888 | 0.2418 | 0.2958 | 0.060* | |
| C15 | 0.2393 (4) | 0.20147 (11) | 0.33483 (10) | 0.0453 (7) | |
| H15 | 0.1790 | 0.1722 | 0.3322 | 0.054* | |
| C16 | 0.3810 (3) | 0.20282 (9) | 0.36059 (8) | 0.0326 (6) | |
| H16 | 0.4178 | 0.1744 | 0.3755 | 0.039* | |
| C1 | 0.6212 (3) | 0.24786 (8) | 0.39198 (6) | 0.0222 (4) | |
| O1 | 0.7037 (2) | 0.28433 (5) | 0.39542 (5) | 0.0300 (4) | |
| C2 | 0.6774 (3) | 0.20274 (8) | 0.41744 (7) | 0.0220 (5) | |
| C21 | 0.6542 (3) | 0.20065 (8) | 0.46670 (6) | 0.0234 (5) | |
| C22 | 0.5622 (3) | 0.23566 (9) | 0.48904 (7) | 0.0291 (5) | |
| H22 | 0.5110 | 0.2608 | 0.4723 | 0.035* | |
| C23 | 0.5449 (3) | 0.23409 (10) | 0.53561 (8) | 0.0344 (6) | |
| H23 | 0.4825 | 0.2582 | 0.5507 | 0.041* | |
| C24 | 0.6182 (3) | 0.19755 (11) | 0.55991 (8) | 0.0401 (6) | |
| H24 | 0.6067 | 0.1966 | 0.5917 | 0.048* | |
| C25 | 0.7083 (4) | 0.16228 (11) | 0.53816 (8) | 0.0406 (7) | |
| H25 | 0.7575 | 0.1369 | 0.5550 | 0.049* | |
| C26 | 0.7272 (3) | 0.16376 (9) | 0.49169 (8) | 0.0332 (6) | |
| H26 | 0.7901 | 0.1396 | 0.4769 | 0.040* | |
| N1 | 0.7555 (2) | 0.16872 (7) | 0.39690 (6) | 0.0265 (4) | |
| N2 | 0.7675 (2) | 0.17867 (7) | 0.35026 (6) | 0.0255 (4) | |
| C3 | 0.8450 (3) | 0.14520 (8) | 0.32965 (7) | 0.0245 (5) | |
| H3 | 0.8903 | 0.1192 | 0.3465 | 0.029* | |
| C31 | 0.8657 (3) | 0.14596 (8) | 0.28078 (7) | 0.0252 (5) | |
| C32 | 0.9510 (3) | 0.10863 (9) | 0.25997 (8) | 0.0307 (5) | |
| H32 | 0.9991 | 0.0838 | 0.2777 | 0.037* | |
| C33 | 0.9664 (3) | 0.10743 (10) | 0.21338 (8) | 0.0383 (6) | |
| H33 | 1.0228 | 0.0814 | 0.1993 | 0.046* | |
| C34 | 0.9002 (3) | 0.14389 (9) | 0.18749 (8) | 0.0371 (6) | |
| H34 | 0.9115 | 0.1431 | 0.1556 | 0.045* | |
| C35 | 0.8166 (3) | 0.18203 (10) | 0.20799 (8) | 0.0346 (6) | |
| H35 | 0.7721 | 0.2074 | 0.1902 | 0.041* | |
| C36 | 0.7987 (3) | 0.18291 (9) | 0.25427 (8) | 0.0294 (5) | |
| H36 | 0.7406 | 0.2087 | 0.2682 | 0.035* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C11 | 0.0250 (11) | 0.0314 (12) | 0.0200 (9) | 0.0026 (11) | 0.0015 (8) | 0.0014 (8) |
| C12 | 0.0328 (13) | 0.0337 (13) | 0.0283 (11) | 0.0066 (11) | −0.0003 (10) | 0.0044 (10) |
| C13 | 0.0368 (15) | 0.0525 (17) | 0.0385 (14) | 0.0136 (14) | −0.0061 (11) | 0.0126 (12) |
| C14 | 0.0283 (15) | 0.076 (2) | 0.0472 (15) | −0.0018 (15) | −0.0157 (12) | 0.0105 (15) |
| C15 | 0.0348 (15) | 0.0542 (17) | 0.0471 (15) | −0.0116 (14) | −0.0096 (12) | 0.0049 (13) |
| C16 | 0.0298 (13) | 0.0375 (14) | 0.0304 (11) | −0.0016 (12) | −0.0019 (9) | 0.0049 (10) |
| C1 | 0.0268 (11) | 0.0233 (11) | 0.0166 (8) | 0.0035 (10) | 0.0021 (8) | −0.0012 (8) |
| O1 | 0.0370 (10) | 0.0233 (8) | 0.0298 (8) | −0.0021 (8) | −0.0063 (7) | 0.0013 (6) |
| C2 | 0.0214 (11) | 0.0228 (10) | 0.0217 (9) | −0.0008 (10) | −0.0023 (8) | 0.0004 (8) |
| C21 | 0.0236 (12) | 0.0262 (11) | 0.0205 (9) | −0.0027 (9) | −0.0012 (8) | 0.0029 (8) |
| C22 | 0.0292 (13) | 0.0311 (13) | 0.0268 (11) | 0.0028 (11) | 0.0008 (9) | 0.0009 (9) |
| C23 | 0.0317 (14) | 0.0428 (15) | 0.0288 (12) | 0.0041 (12) | 0.0054 (10) | −0.0010 (10) |
| C24 | 0.0344 (14) | 0.0655 (18) | 0.0203 (10) | 0.0006 (14) | 0.0028 (10) | 0.0063 (12) |
| C25 | 0.0372 (15) | 0.0549 (17) | 0.0297 (12) | 0.0075 (14) | −0.0009 (10) | 0.0153 (11) |
| C26 | 0.0347 (14) | 0.0367 (14) | 0.0284 (12) | 0.0061 (12) | 0.0004 (10) | 0.0079 (10) |
| N1 | 0.0320 (11) | 0.0263 (10) | 0.0212 (9) | 0.0019 (9) | −0.0025 (8) | 0.0019 (7) |
| N2 | 0.0317 (11) | 0.0248 (10) | 0.0201 (9) | 0.0012 (9) | −0.0014 (8) | −0.0013 (7) |
| C3 | 0.0258 (12) | 0.0213 (11) | 0.0265 (10) | −0.0013 (10) | −0.0021 (8) | 0.0005 (9) |
| C31 | 0.0237 (12) | 0.0250 (11) | 0.0268 (10) | −0.0049 (10) | −0.0009 (9) | −0.0034 (9) |
| C32 | 0.0327 (14) | 0.0296 (12) | 0.0299 (12) | 0.0014 (11) | 0.0035 (9) | −0.0009 (9) |
| C33 | 0.0395 (16) | 0.0419 (15) | 0.0335 (13) | −0.0008 (13) | 0.0100 (10) | −0.0070 (11) |
| C34 | 0.0386 (15) | 0.0490 (16) | 0.0238 (10) | −0.0104 (13) | 0.0031 (10) | −0.0019 (10) |
| C35 | 0.0359 (14) | 0.0378 (14) | 0.0299 (12) | −0.0038 (12) | −0.0064 (10) | 0.0054 (10) |
| C36 | 0.0319 (13) | 0.0256 (12) | 0.0307 (11) | −0.0002 (11) | −0.0049 (10) | 0.0005 (9) |
Geometric parameters (Å, º)
| C11—C16 | 1.390 (3) | C23—H23 | 0.9500 |
| C11—C12 | 1.397 (3) | C24—C25 | 1.381 (4) |
| C11—C1 | 1.483 (3) | C24—H24 | 0.9500 |
| C12—C13 | 1.382 (4) | C25—C26 | 1.388 (3) |
| C12—H12 | 0.9500 | C25—H25 | 0.9500 |
| C13—C14 | 1.382 (4) | C26—H26 | 0.9500 |
| C13—H13 | 0.9500 | N1—N2 | 1.415 (2) |
| C14—C15 | 1.377 (4) | N2—C3 | 1.276 (3) |
| C14—H14 | 0.9500 | C3—C31 | 1.461 (3) |
| C15—C16 | 1.387 (4) | C3—H3 | 0.9500 |
| C15—H15 | 0.9500 | C31—C32 | 1.389 (3) |
| C16—H16 | 0.9500 | C31—C36 | 1.400 (3) |
| C1—O1 | 1.216 (3) | C32—C33 | 1.389 (3) |
| C1—C2 | 1.528 (3) | C32—H32 | 0.9500 |
| C2—N1 | 1.288 (3) | C33—C34 | 1.377 (4) |
| C2—C21 | 1.476 (3) | C33—H33 | 0.9500 |
| C21—C22 | 1.392 (3) | C34—C35 | 1.395 (4) |
| C21—C26 | 1.394 (3) | C34—H34 | 0.9500 |
| C22—C23 | 1.390 (3) | C35—C36 | 1.382 (3) |
| C22—H22 | 0.9500 | C35—H35 | 0.9500 |
| C23—C24 | 1.377 (4) | C36—H36 | 0.9500 |
| C16—C11—C12 | 119.5 (2) | C23—C24—C25 | 120.2 (2) |
| C16—C11—C1 | 121.1 (2) | C23—C24—H24 | 119.9 |
| C12—C11—C1 | 119.4 (2) | C25—C24—H24 | 119.9 |
| C13—C12—C11 | 119.7 (2) | C24—C25—C26 | 120.2 (2) |
| C13—C12—H12 | 120.1 | C24—C25—H25 | 119.9 |
| C11—C12—H12 | 120.1 | C26—C25—H25 | 119.9 |
| C12—C13—C14 | 120.3 (2) | C25—C26—C21 | 120.2 (2) |
| C12—C13—H13 | 119.9 | C25—C26—H26 | 119.9 |
| C14—C13—H13 | 119.9 | C21—C26—H26 | 119.9 |
| C15—C14—C13 | 120.4 (2) | C2—N1—N2 | 110.84 (16) |
| C15—C14—H14 | 119.8 | C3—N2—N1 | 111.29 (17) |
| C13—C14—H14 | 119.8 | N2—C3—C31 | 121.5 (2) |
| C14—C15—C16 | 119.8 (3) | N2—C3—H3 | 119.2 |
| C14—C15—H15 | 120.1 | C31—C3—H3 | 119.2 |
| C16—C15—H15 | 120.1 | C32—C31—C36 | 119.1 (2) |
| C15—C16—C11 | 120.2 (2) | C32—C31—C3 | 119.3 (2) |
| C15—C16—H16 | 119.9 | C36—C31—C3 | 121.6 (2) |
| C11—C16—H16 | 119.9 | C31—C32—C33 | 120.4 (2) |
| O1—C1—C11 | 122.96 (19) | C31—C32—H32 | 119.8 |
| O1—C1—C2 | 117.85 (19) | C33—C32—H32 | 119.8 |
| C11—C1—C2 | 119.19 (19) | C34—C33—C32 | 120.2 (2) |
| N1—C2—C21 | 120.24 (19) | C34—C33—H33 | 119.9 |
| N1—C2—C1 | 120.61 (18) | C32—C33—H33 | 119.9 |
| C21—C2—C1 | 118.91 (18) | C33—C34—C35 | 120.1 (2) |
| C22—C21—C26 | 118.99 (19) | C33—C34—H34 | 120.0 |
| C22—C21—C2 | 120.9 (2) | C35—C34—H34 | 120.0 |
| C26—C21—C2 | 120.1 (2) | C36—C35—C34 | 119.9 (2) |
| C23—C22—C21 | 120.4 (2) | C36—C35—H35 | 120.0 |
| C23—C22—H22 | 119.8 | C34—C35—H35 | 120.0 |
| C21—C22—H22 | 119.8 | C35—C36—C31 | 120.3 (2) |
| C24—C23—C22 | 120.0 (2) | C35—C36—H36 | 119.8 |
| C24—C23—H23 | 120.0 | C31—C36—H36 | 119.8 |
| C22—C23—H23 | 120.0 | ||
| C16—C11—C12—C13 | 0.7 (3) | C2—C21—C22—C23 | −178.2 (2) |
| C1—C11—C12—C13 | 179.7 (2) | C21—C22—C23—C24 | −0.4 (4) |
| C11—C12—C13—C14 | 0.2 (4) | C22—C23—C24—C25 | −0.3 (4) |
| C12—C13—C14—C15 | −1.0 (4) | C23—C24—C25—C26 | 0.8 (4) |
| C13—C14—C15—C16 | 0.7 (5) | C24—C25—C26—C21 | −0.5 (4) |
| C14—C15—C16—C11 | 0.2 (4) | C22—C21—C26—C25 | −0.2 (4) |
| C12—C11—C16—C15 | −1.0 (3) | C2—C21—C26—C25 | 178.7 (2) |
| C1—C11—C16—C15 | −179.9 (2) | C21—C2—N1—N2 | −178.27 (18) |
| C16—C11—C1—O1 | 178.1 (2) | C1—C2—N1—N2 | −3.8 (3) |
| C12—C11—C1—O1 | −0.8 (3) | C2—N1—N2—C3 | 179.9 (2) |
| C16—C11—C1—C2 | −2.4 (3) | N1—N2—C3—C31 | 176.64 (19) |
| C12—C11—C1—C2 | 178.7 (2) | N2—C3—C31—C32 | −180.0 (2) |
| O1—C1—C2—N1 | −100.0 (2) | N2—C3—C31—C36 | −1.3 (3) |
| C11—C1—C2—N1 | 80.6 (3) | C36—C31—C32—C33 | −1.4 (4) |
| O1—C1—C2—C21 | 74.6 (3) | C3—C31—C32—C33 | 177.3 (2) |
| C11—C1—C2—C21 | −104.9 (2) | C31—C32—C33—C34 | 1.5 (4) |
| N1—C2—C21—C22 | −176.3 (2) | C32—C33—C34—C35 | −0.4 (4) |
| C1—C2—C21—C22 | 9.1 (3) | C33—C34—C35—C36 | −0.7 (4) |
| N1—C2—C21—C26 | 4.9 (3) | C34—C35—C36—C31 | 0.7 (4) |
| C1—C2—C21—C26 | −169.7 (2) | C32—C31—C36—C35 | 0.4 (4) |
| C26—C21—C22—C23 | 0.6 (4) | C3—C31—C36—C35 | −178.3 (2) |
Hydrogen-bond geometry (Å, º)
Cg is the centroid of the C31–C36 phenyl ring.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C35—H35···O1i | 0.95 | 2.61 | 3.337 (3) | 134 |
| C3—H3···O1ii | 0.95 | 2.41 | 3.272 (3) | 151 |
| C32—H32···O1ii | 0.95 | 2.68 | 3.478 (3) | 141 |
| C26—H26···Cgiii | 0.95 | 2.97 | 3.699 (3) | 135 |
Symmetry codes: (i) x, −y+1/2, −z+1/2; (ii) x+1/4, y−1/4, −z+3/4; (iii) x+1/4, −y+1/4, z+1/4.
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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. DOI: 10.1107/S2056989014026358/su5029sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014026358/su5029Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989014026358/su5029Isup3.cml
CCDC reference: 1036846
Additional supporting information: crystallographic information; 3D view; checkCIF report