Crystal structure of (Z)-2-[(E)-2-benzyl­idene­hydrazin-1-yl­idene]-1,2-di­phenyl­ethanone

Bouchama, A.; Yahiaoui, M.; Chiter, C.; Setifi, Z.; Simpson, J.

doi:10.1107/S2056989014026358

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 1| January 2015| Pages 35-37

https://doi.org/10.1107/S2056989014026358

Open

access

Crystal structure of (Z)-2-[(E)-2-benzylidenehydrazin-1-ylidene]-1,2-diphenylethanone

Abdelaziz Bouchama,^a Messaoud Yahiaoui,^b Chaabane Chiter,^b Zouaoui Setifi ^c,^a ^* and Jim Simpson ^d

^aLaboratoire de Chimie, Ingénierie Moléculaire et Nanostructures (LCIMN), Université Ferhat Abbas Sétif 1, Sétif 19000, Algeria, ^bLaboratoire d'Electrochimie des Matériaux Moléculaires et Complexes (L.E.M.M.C.), Université Ferhat Abbas Sétif 1, Sétif 19000, Algeria, ^cDépartement de Technologie, Faculté de Technologie, Université 20 Août 1955-Skikda, BP 26, Route d'El-Hadaiek, Skikda 21000, Algeria, and ^dDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
^*Correspondence e-mail: setifi_zouaoui@yahoo.fr

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 21 November 2014; accepted 1 December 2014; online 1 January 2015)

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.

Keywords: crystal structure; Schiff base; azines; dimers; C—H⋯π contacts.

CCDC reference: 1036846

1. 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.

2. 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.

3. Supramolecular features

In the crystal, a pair of C35—H35⋯O1 hydrogen bonds link adjacent molecules into dimers with R₂²(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 R₂¹(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.

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x, -y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 4}}, y-{\script{1\over 4}}, -z+{\script{3\over 4}}]$ ; (iii) $[x+{\script{1\over 4}}, -y+{\script{1\over 4}}, z+{\script{1\over 4}}]$ .

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.

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).

4. 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)

5. 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%.

6. 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, F2dd
Temperature (K)	150
a, b, c (Å)	8.1653 (3), 27.6113 (11), 29.6818 (13)
V (Å³)	6691.9 (5)
Z	16
Radiation type	Mo Kα
μ (mm⁻¹)	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 > 2σ(I)] reflections	8049, 3350, 3036
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), 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
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.16
Computer programs: APEX2 and SAINT (Bruker, 2006), SIR97 (Altomare et al., 1999 ), SHELXL2014 (Sheldrick, 2008 ), Mercury (Macrae et al., 2008 ), CRYSCAL (T. Roisnel, local program), enCIFer (Allen et al., 2004 ), PLATON (Spek, 2009 ), WinGX (Farrugia, 2012 ) and publCIF (Westrip 2010 ).

Supporting information

CCDC reference: 1036846

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989014026358/su5029sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989014026358/su5029Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989014026358/su5029Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: CRYSCAL (T. Roisnel, local program), SHELXL2014 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009), publCIF (Westrip 2010) and WinGX (Farrugia, 2012).

(Z)-2-[(E)-2-Benzylidenehydrazin-1-ylidene]-1,2-diphenylethanone top

Crystal data top

C₂₁H₁₆N₂O	F(000) = 2624
M_r = 312.36	D_x = 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 top

Bruker APEXII diffractometer	3036 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
CCD rotation images, thin slices scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −9→10
T_min = 0.884, T_max = 0.982	k = −35→24
8049 measured reflections	l = −38→38
3350 independent reflections

Refinement top

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(F_o²) + (0.0407P)² + 4.1058P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3350 reflections	Δρ_max = 0.18 e Å⁻³
217 parameters	Δρ_min = −0.16 e Å⁻³

Special details top

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) top

	x	y	z	U_iso*/U_eq
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) top

	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) top

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) top

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.

Acknowledgements

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.

References

Abbasi, A., Mohammadi Ziarani, G. & Tarighi, S. (2007). Acta Cryst. E63, o2579–o2580. Web of Science CSD CrossRef IUCr Journals Google Scholar
Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dudis, D. S., Yeates, A. T., Kost, D., Smith, D. A. & Medrano, J. (1993). J. Am. Chem. Soc. 115, 8770–8774. CrossRef CAS Web of Science Google Scholar
Facchetti, A., Abbotto, A., Beverina, L., van der Boom, M. E., Dutta, P., Evmenenko, G., Marks, T. J. & Pagani, G. A. (2002). Chem. Mater. 14, 4996–5005. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662–671. Web of Science CSD CrossRef CAS Google Scholar
Kim, S. H., Gwon, S. Y., Burkinshaw, S. M. & Son, Y. A. (2010). Dyes Pigm. 87, 268–271. Web of Science CrossRef CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Pandeya, S. N., Sriram, D., Nath, G. & De Clercq, E. (1999). Pharm. Acta Helv. 74, 11–17. CrossRef PubMed CAS Google Scholar
Patra, G. K., Mukherjee, A. & Ng, S. W. (2009). Acta Cryst. E65, o1745. Web of Science CSD CrossRef IUCr Journals Google Scholar
Patra, G. K. & Ng, S. W. (2009). Acta Cryst. E65, o1810. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wadher, J. S., Puranik, M. P., Karande, N. A. & Yeole, P. G. (2009). J. Pharm. Tech. Res. 1, 22–33. CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wieland, M., Seichter, W., Schwarzer, A. & Weber, E. (2011). Struct. Chem. 22, 1267–1279. Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.