organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

N′-[(E)-Benzyl­­idene]-2-(6-meth­­oxy­naphthalen-2-yl)propano­hydrazide

aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, dChemistry Department, Faculty of Science, Mini University, 61519 El-Minia, Egypt, eDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com

(Received 30 September 2013; accepted 1 October 2013; online 5 October 2013)

The title mol­ecule, C21H20N2O2, exists in the solid state in the `extended' form. The crystal packing consists of ribbons of mol­ecules extending parallel to c and associated via N—H⋯O and weak C—H⋯O hydrogen bonds. C—H⋯π inter­actions are also present.

Related literature

For general clinical use of nonsteroidal anti-inflammatory drugs (NSAIDs) and Naproxen®, see: Merlet et al. (2013[Merlet, N., Busseuil, D., Rhéaume, E. & Tardif, J.-C. (2013). Anti-Inflammatory Anti-Allergy Agents Med. Chem. 12, 24-35.]); Khanna et al. (2006[Khanna, S., Madan, M., Vangoori, A., Banerjee, R., Thaimattam, R., Sadik, J., Basha, S. K., Ramesh, M., Casturi, S. R. & Pal, M. (2006). Bioorg. Med. Chem. 14, 4820-4833.]); Bhaduri et al. (1995[Bhaduri, J., Hota, D. & Acharya, S. B. (1995). Indian J. Exp. Biol. 33, 667-681.]); Dharmani et al. (2004[Dharmani, P., Kuchibhotla, V. K., Maurya, R., Srivatsava, S., Sharma, S. & Palit, G. (2004). J. Ethnopharmacol. 93, 197-206.]). For common side effects of NSAIDs, see: Neeraj et al. (2010[Neeraj, A., Chandrasekar, M. J. N., Sara, U. V. S. & Rohini, A. (2010). Int. J. Drug Delivery Technol. 2, 12-17.]); Asif (2009[Asif, H. (2009). Acta Pol. Pharm. Drug Res. 66, 513-521.]); Parmeshwari et al. (2009[Parmeshwari, K. H., Murumkar, P. R., Giridhar, R. & Yadav, M. R. (2009). Mini Rev. Med. Chem. 9, 124-139.]).

[Scheme 1]

Experimental

Crystal data
  • C21H20N2O2

  • Mr = 332.39

  • Orthorhombic, P 21 21 21

  • a = 10.3754 (17) Å

  • b = 32.519 (5) Å

  • c = 5.0615 (8) Å

  • V = 1707.7 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 150 K

  • 0.15 × 0.11 × 0.11 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.73, Tmax = 0.99

  • 28152 measured reflections

  • 4230 independent reflections

  • 3882 reflections with I > 2σ(I)

  • Rint = 0.053

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.128

  • S = 1.10

  • 4230 reflections

  • 232 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C4–C9 benzene and C16–C21 phenyl rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2i 0.94 (3) 1.98 (4) 2.892 (3) 163 (3)
C15—H15⋯O2i 0.95 2.49 3.261 (3) 138
C18—H18⋯O1ii 0.95 2.59 3.209 (4) 123
C1—H1CCg3iii 0.98 2.91 3.696 (3) 138
C12—H12⋯Cg2i 1.00 2.78 3.661 (3) 147
Symmetry codes: (i) x, y, z-1; (ii) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Anti-inflammatory drugs are widely prescribed in clinical practice to treat a broad range of diseases associated with inflammatory processes (Merlet et al., 2013). Naproxen, (S)-(+)-6-methoxy-a-methyl-2-naphthaleneacetic acid, is a non-steroidal anti-inflammatory drug used in painful inflammatory rheumatic and certain non-rheumatic conditions (Khanna et al., 2006; Bhaduri et al., 1995; Dharmani et al., 2004). As with other common non-steroidal anti-inflammatory drugs (NSAIDs), Naproxen has been reported to be associated with a number of undesirable effects, which in particular include gastrointestinal (GI) toxicity (Neeraj et al., 2010). These reports confirm that gastrointestinal side-effects are due to the presence of a free carboxylic group (Asif 2009). Therefore, temporary masking or manipulation of the acidic group in NSAIDs are promising means to reduce or to abolish the GI toxicity due to the local action mechanism (Parmeshwari et al., 2009). Based on such facts, the title compound has been prepared.

In the title molecule (Fig. 1), the naphthalene ring system (C2–C11) is essentially planar with an r.m.s. deviation of 0.003 Å and makes a dihedral angle of 77.57 (12)° with the terminal phenyl ring (C16–C21).

In the crystal structure, the molecules exist in the "extended" form. The packing consists of ribbons of molecules extending parallel to c (Fig. 2) and associated via N—H···O and weak C—H···O hydrogen bonds (Table 1 and Fig. 3). In addition, C—H···p interactions are observed (Table 1).

Related literature top

For general clinical use of nonsteroidal anti-inflammatory drugs (NSAIDs) and Naproxen, see: Merlet et al. (2013); Khanna et al. (2006); Bhaduri et al. (1995); Dharmani et al. (2004). For common side effects of NSAIDs, see: (Neeraj et al. (2010); Asif (2009); Parmeshwari et al. (2009).

Experimental top

A mixture of 244 mg (1 mmol) of 2-(6-methoxynaphthalen-2-yl)propanehydrazide and benzaldehyde 106 mg (1 mmol) in 30 ml ethanol with few drops of glacial acetic acid as a catalyst was refluxed for 5 h. After the reaction mixture was cooled to ambient temperature, the excess solvent was evaporated under vacuum and the resulting solid product was filtered off, washed with cold ethanol and recrystallized from ethanol to afford high quality, clear colourless blocks (M.p. 453 – 455 K) in a good yield 79%..

Refinement top

The amino H atom was located in a difference Fourier map and was refined with Uiso(H) = 1.2Ueq(N). C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms with C—H = 0.95 - 1.00 Å, with Uiso(H) = 1.2 or 1.5Uiso(C).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXTL (Bruker, 2013); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Perspective view of the title molecule with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The hydrogen bonding (dotted lines) viewed along the a axis of the title compound.
[Figure 3] Fig. 3. Packing viewed along the c axis showing the ribbon like structure with intra-ribbon C—H···O hydrogen bonds.
N'-[(E)-Benzylidene]-2-(6-methoxynaphthalen-2-yl)propanohydrazide top
Crystal data top
C21H20N2O2F(000) = 704
Mr = 332.39Dx = 1.293 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 9954 reflections
a = 10.3754 (17) Åθ = 2.3–28.2°
b = 32.519 (5) ŵ = 0.08 mm1
c = 5.0615 (8) ÅT = 150 K
V = 1707.7 (5) Å3Block, clear colourless
Z = 40.15 × 0.11 × 0.11 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
4230 independent reflections
Radiation source: fine-focus sealed tube3882 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
Detector resolution: 8.3660 pixels mm-1θmax = 28.3°, θmin = 2.1°
ϕ and ω scansh = 1313
Absorption correction: multi-scan
SADABS (Bruker, 2013)
k = 4342
Tmin = 0.73, Tmax = 0.99l = 66
28152 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.128 w = 1/[Σ2(Fo2) + (0.0416P)2 + 1.3067P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
4230 reflectionsΔρmax = 0.34 e Å3
232 parametersΔρmin = 0.26 e Å3
0 restraints
Crystal data top
C21H20N2O2V = 1707.7 (5) Å3
Mr = 332.39Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 10.3754 (17) ŵ = 0.08 mm1
b = 32.519 (5) ÅT = 150 K
c = 5.0615 (8) Å0.15 × 0.11 × 0.11 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
4230 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 2013)
3882 reflections with I > 2σ(I)
Tmin = 0.73, Tmax = 0.99Rint = 0.053
28152 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.128H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.34 e Å3
4230 reflectionsΔρmin = 0.26 e Å3
232 parameters
Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at ϕ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in ϕ, collected at ω = -30.00 and 210.00°. The scan time was 25 sec/frame.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.8923 (2)0.05817 (7)1.2997 (5)0.0341 (7)
O21.0001 (3)0.28050 (6)0.4958 (4)0.0327 (7)
N10.9781 (2)0.29446 (7)0.0582 (5)0.0212 (7)
N20.9700 (2)0.33651 (7)0.0988 (5)0.0217 (6)
C10.7617 (3)0.05673 (11)1.3868 (7)0.0360 (10)
C20.9231 (3)0.08584 (8)1.1061 (6)0.0251 (8)
C30.8391 (3)0.11238 (8)0.9855 (6)0.0236 (8)
C40.8842 (3)0.13987 (8)0.7876 (6)0.0206 (8)
C50.8006 (3)0.16752 (9)0.6535 (6)0.0233 (8)
C60.8471 (3)0.19367 (8)0.4643 (6)0.0234 (8)
C70.9800 (3)0.19449 (8)0.3953 (6)0.0206 (7)
C81.0616 (3)0.16783 (8)0.5222 (6)0.0222 (7)
C91.0170 (3)0.13986 (8)0.7169 (6)0.0213 (7)
C101.1001 (3)0.11197 (9)0.8480 (6)0.0255 (8)
C111.0553 (3)0.08558 (9)1.0365 (6)0.0270 (8)
C121.0243 (3)0.22433 (8)0.1836 (6)0.0216 (7)
C131.1682 (3)0.22119 (9)0.1119 (7)0.0282 (8)
C140.9980 (3)0.26884 (8)0.2669 (5)0.0203 (7)
C150.9435 (3)0.35759 (8)0.1088 (6)0.0222 (8)
C160.9384 (3)0.40269 (8)0.0976 (6)0.0222 (7)
C170.9991 (3)0.42472 (9)0.1062 (6)0.0261 (8)
C180.9965 (3)0.46725 (9)0.1063 (7)0.0307 (9)
C190.9334 (3)0.48871 (9)0.0913 (7)0.0316 (9)
C200.8714 (3)0.46720 (10)0.2899 (7)0.0316 (9)
C210.8748 (3)0.42453 (10)0.2946 (7)0.0286 (9)
H10.976 (3)0.2849 (10)0.117 (7)0.025 (8)*
H1A0.735400.084001.448800.0540*
H1B0.753700.036901.531700.0540*
H1C0.706100.048301.239900.0540*
H30.750700.112401.034100.0280*
H50.711400.167900.695700.0280*
H60.789200.211700.376800.0280*
H81.150600.168100.478400.0270*
H101.189000.111600.803600.0310*
H111.112800.067101.121100.0320*
H120.973200.218700.020000.0260*
H13A1.220500.227100.268600.0420*
H13B1.188400.241100.027100.0420*
H13C1.187200.193400.048500.0420*
H150.927100.343900.271100.0270*
H171.041900.410400.244200.0310*
H181.038700.481900.243700.0370*
H190.932600.517900.090500.0380*
H200.826200.481700.423900.0380*
H210.833200.410100.433800.0340*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0352 (12)0.0320 (12)0.0351 (12)0.0008 (10)0.0024 (10)0.0129 (10)
O20.0526 (15)0.0248 (10)0.0207 (10)0.0008 (10)0.0018 (10)0.0023 (8)
N10.0266 (12)0.0207 (11)0.0162 (11)0.0018 (9)0.0001 (9)0.0013 (9)
N20.0218 (11)0.0211 (11)0.0223 (11)0.0016 (9)0.0007 (10)0.0015 (9)
C10.0376 (17)0.0389 (18)0.0314 (17)0.0073 (14)0.0031 (15)0.0077 (15)
C20.0324 (15)0.0198 (13)0.0230 (13)0.0012 (11)0.0018 (12)0.0017 (11)
C30.0209 (13)0.0216 (13)0.0283 (15)0.0007 (10)0.0017 (11)0.0002 (11)
C40.0220 (13)0.0177 (13)0.0220 (13)0.0001 (10)0.0000 (11)0.0012 (10)
C50.0176 (12)0.0234 (13)0.0290 (16)0.0029 (10)0.0003 (11)0.0017 (11)
C60.0217 (13)0.0218 (13)0.0267 (15)0.0039 (10)0.0012 (11)0.0020 (11)
C70.0223 (12)0.0176 (12)0.0218 (12)0.0002 (9)0.0028 (11)0.0017 (10)
C80.0179 (12)0.0245 (13)0.0242 (13)0.0000 (10)0.0020 (11)0.0023 (11)
C90.0215 (13)0.0197 (12)0.0227 (13)0.0011 (10)0.0004 (11)0.0017 (10)
C100.0200 (13)0.0293 (15)0.0271 (16)0.0055 (11)0.0002 (12)0.0004 (11)
C110.0296 (15)0.0272 (14)0.0243 (15)0.0073 (11)0.0042 (12)0.0033 (11)
C120.0228 (13)0.0206 (12)0.0213 (13)0.0018 (10)0.0009 (11)0.0015 (10)
C130.0259 (14)0.0268 (14)0.0319 (16)0.0001 (11)0.0069 (13)0.0007 (13)
C140.0208 (13)0.0236 (13)0.0164 (12)0.0027 (10)0.0034 (10)0.0014 (10)
C150.0203 (12)0.0257 (14)0.0205 (13)0.0023 (10)0.0002 (11)0.0021 (11)
C160.0183 (12)0.0242 (13)0.0241 (13)0.0002 (10)0.0025 (11)0.0009 (11)
C170.0247 (14)0.0271 (14)0.0265 (13)0.0003 (11)0.0023 (12)0.0003 (12)
C180.0335 (16)0.0269 (15)0.0316 (15)0.0025 (12)0.0001 (14)0.0045 (12)
C190.0348 (17)0.0204 (14)0.0397 (18)0.0039 (11)0.0070 (15)0.0009 (13)
C200.0292 (16)0.0324 (17)0.0333 (16)0.0065 (12)0.0008 (13)0.0066 (13)
C210.0251 (14)0.0320 (16)0.0286 (15)0.0002 (11)0.0035 (12)0.0013 (13)
Geometric parameters (Å, º) top
O1—C11.426 (4)C17—C181.383 (4)
O1—C21.368 (4)C18—C191.384 (5)
O2—C141.219 (3)C19—C201.383 (5)
N1—N21.385 (3)C20—C211.388 (5)
N1—C141.361 (4)C1—H1A0.9800
N2—C151.284 (4)C1—H1B0.9800
N1—H10.94 (3)C1—H1C0.9800
C2—C111.416 (4)C3—H30.9500
C2—C31.370 (4)C5—H50.9500
C3—C41.422 (4)C6—H60.9500
C4—C91.424 (4)C8—H80.9500
C4—C51.422 (4)C10—H100.9500
C5—C61.369 (4)C11—H110.9500
C6—C71.423 (4)C12—H121.0000
C7—C121.517 (4)C13—H13A0.9800
C7—C81.372 (4)C13—H13B0.9800
C8—C91.419 (4)C13—H13C0.9800
C9—C101.416 (4)C15—H150.9500
C10—C111.365 (4)C17—H170.9500
C12—C131.540 (4)C18—H180.9500
C12—C141.532 (4)C19—H190.9500
C15—C161.469 (4)C20—H200.9500
C16—C211.391 (4)C21—H210.9500
C16—C171.405 (4)
C1—O1—C2117.7 (2)O1—C1—H1B109.00
N2—N1—C14119.9 (2)O1—C1—H1C110.00
N1—N2—C15114.7 (2)H1A—C1—H1B109.00
C14—N1—H1122 (2)H1A—C1—H1C109.00
N2—N1—H1118 (2)H1B—C1—H1C109.00
O1—C2—C11113.6 (3)C2—C3—H3120.00
O1—C2—C3125.8 (3)C4—C3—H3120.00
C3—C2—C11120.6 (3)C4—C5—H5120.00
C2—C3—C4120.0 (3)C6—C5—H5120.00
C5—C4—C9118.1 (3)C5—C6—H6119.00
C3—C4—C9119.7 (3)C7—C6—H6119.00
C3—C4—C5122.2 (3)C7—C8—H8119.00
C4—C5—C6120.8 (3)C9—C8—H8119.00
C5—C6—C7121.7 (3)C9—C10—H10119.00
C6—C7—C12118.6 (3)C11—C10—H10119.00
C6—C7—C8118.1 (3)C2—C11—H11120.00
C8—C7—C12123.2 (3)C10—C11—H11120.00
C7—C8—C9122.0 (3)C7—C12—H12108.00
C4—C9—C10118.1 (3)C13—C12—H12108.00
C4—C9—C8119.4 (3)C14—C12—H12108.00
C8—C9—C10122.5 (3)C12—C13—H13A109.00
C9—C10—C11121.5 (3)C12—C13—H13B109.00
C2—C11—C10120.0 (3)C12—C13—H13C109.00
C13—C12—C14107.5 (2)H13A—C13—H13B109.00
C7—C12—C14110.9 (2)H13A—C13—H13C110.00
C7—C12—C13114.7 (2)H13B—C13—H13C109.00
O2—C14—C12123.5 (2)N2—C15—H15120.00
O2—C14—N1123.4 (2)C16—C15—H15120.00
N1—C14—C12113.1 (2)C16—C17—H17120.00
N2—C15—C16120.6 (3)C18—C17—H17120.00
C15—C16—C17121.4 (3)C17—C18—H18120.00
C17—C16—C21118.6 (3)C19—C18—H18120.00
C15—C16—C21120.0 (3)C18—C19—H19120.00
C16—C17—C18120.1 (3)C20—C19—H19120.00
C17—C18—C19120.9 (3)C19—C20—H20120.00
C18—C19—C20119.4 (3)C21—C20—H20120.00
C19—C20—C21120.4 (3)C16—C21—H21120.00
C16—C21—C20120.7 (3)C20—C21—H21120.00
O1—C1—H1A110.00
C1—O1—C2—C30.5 (4)C6—C7—C12—C13176.7 (3)
C1—O1—C2—C11178.8 (3)C6—C7—C12—C1461.4 (3)
C14—N1—N2—C15176.1 (3)C8—C7—C12—C132.6 (4)
N2—N1—C14—O25.6 (4)C8—C7—C12—C14119.4 (3)
N2—N1—C14—C12171.5 (2)C7—C8—C9—C41.3 (4)
N1—N2—C15—C16176.9 (2)C7—C8—C9—C10179.5 (3)
O1—C2—C3—C4179.6 (3)C4—C9—C10—C110.2 (4)
C11—C2—C3—C40.3 (4)C8—C9—C10—C11179.4 (3)
O1—C2—C11—C10179.2 (3)C9—C10—C11—C20.4 (5)
C3—C2—C11—C100.1 (4)C7—C12—C14—O231.6 (4)
C2—C3—C4—C5178.9 (3)C7—C12—C14—N1151.3 (3)
C2—C3—C4—C90.4 (4)C13—C12—C14—O294.4 (4)
C3—C4—C5—C6179.9 (3)C13—C12—C14—N182.6 (3)
C9—C4—C5—C60.8 (4)N2—C15—C16—C1720.1 (5)
C3—C4—C9—C8179.0 (3)N2—C15—C16—C21161.3 (3)
C3—C4—C9—C100.2 (4)C15—C16—C17—C18177.7 (3)
C5—C4—C9—C81.6 (4)C21—C16—C17—C180.9 (5)
C5—C4—C9—C10179.2 (3)C15—C16—C21—C20178.6 (3)
C4—C5—C6—C70.4 (4)C17—C16—C21—C200.0 (5)
C5—C6—C7—C80.7 (4)C16—C17—C18—C190.7 (5)
C5—C6—C7—C12180.0 (3)C17—C18—C19—C200.5 (5)
C6—C7—C8—C90.2 (4)C18—C19—C20—C211.5 (5)
C12—C7—C8—C9179.1 (3)C19—C20—C21—C161.2 (5)
Hydrogen-bond geometry (Å, º) top
Cg2 and Cg3 are the centroids of the C4–C9 benzene and C16–C21 phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.94 (3)1.98 (4)2.892 (3)163 (3)
C15—H15···O2i0.952.493.261 (3)138
C18—H18···O1ii0.952.593.209 (4)123
C1—H1C···Cg3iii0.982.913.696 (3)138
C12—H12···Cg2i1.002.783.661 (3)147
Symmetry codes: (i) x, y, z1; (ii) x+2, y+1/2, z+3/2; (iii) x1/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
Cg2 and Cg3 are the centroids of the C4–C9 benzene and C16–C21 phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.94 (3)1.98 (4)2.892 (3)163 (3)
C15—H15···O2i0.952.493.261 (3)138
C18—H18···O1ii0.952.593.209 (4)123
C1—H1C···Cg3iii0.982.913.696 (3)138
C12—H12···Cg2i1.002.783.661 (3)147
Symmetry codes: (i) x, y, z1; (ii) x+2, y+1/2, z+3/2; (iii) x1/2, y+1/2, z+1.
 

Acknowledgements

The authors thank Tulane University, Manchester Metropolitan University and Erciyes University for supporting this study.

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